Azoline compounds

ABSTRACT

wherein A, B1, B2, B3, G1, G2, X1, R1, R3a, R3b, Rg1 and Rg2 are as defined in the claims and the description. The compounds are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also relates to a method for controlling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.

The present invention relates to azoline compounds which are useful forcombating or controlling invertebrate pests, in particular arthropodpests and nematodes. The invention also relates to a method forcontrolling invertebrate pests by using these compounds and to plantpropagation material and to an agricultural and a veterinary compositioncomprising said compounds.

Invertebrate pests and in particular arthropods and nematodes destroygrowing and harvested crops and attack wooden dwelling and commercialstructures, causing large economic loss to the food supply and toproperty. While a large number of pesticidal agents are known, due tothe ability of target pests to develop resistance to said agents, thereis an on-going need for new agents for combating invertebrate pests, inparticular insects, arachnids and nematodes.

Related compounds are described in WO 2013/026929, WO 2012/163959, WO2012/007426, WO 2011/067272, WO 2010/149506, WO 2010/020522, WO2009/080250, EP-A-1731512, JP-A-2007091708 and JP-A-2008133273. However,these documents do not describe compounds having the characteristicsubstituents and substituents' arrangement as claimed in the presentinvention.

It is an object of the present invention to provide compounds that havea good pesticidal activity, in particular insecticidal activity, andshow a broad activity spectrum against a large number of differentinvertebrate pests, especially against difficult to control arthropodpests and/or nematodes.

The object of the present invention is moreover to provide compoundswhich are less persistent, bioaccumulative and/or toxic than thecompounds of the prior art. Especially isoxazoline insecticides of theprior art show a high persistency in the soil and thus accumulate there.

It has been found that these objectives can be achieved by azolinecompounds of the formula I below, by their stereoisomers and by theirsalts, in particular their agriculturally or veterinarily acceptablesalts.

Therefore, in a first aspect, the invention relates to azoline compoundsof the formula I

wherein

-   X¹ is O or CH₂;-   A is a group of following formula:

wherein

-   -   # denotes the bond to the aromatic ring of formula (I);    -   W is selected from O and S;    -   Y is selected from hydrogen, —N(R⁵)R⁶ and —OR⁹;

-   B¹, B² and B³ are each independently selected from the group    consisting of N and CR², with the proviso that at most two of B¹, B²    and B³ are N;

-   G¹ and G² are each independently selected from the group consisting    of N and CR⁴, with the proviso that at most one of G¹ and G² is N;

-   R^(g1) and R^(g2) form together a bridging group selected from    —CH₂CH₂CH₂CH₂— and —CH₂CH₂CH₂—;

-   R¹ is selected from the group consisting of C₁-C₄-alkyl,    C₁-C₄-haloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,    C₁-C₄-haloalkoxy-C₁-C₄-alkyl-, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl,    C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C₃-C₆-cycloalkyl,    C₃-C₆-halocycloalkyl and —C(═O)OR¹⁵;

-   each R² is independently selected from the group consisting of    hydrogen, halogen, cyano, azido, nitro, —SCN, —SF₅, C₁-C₆-alkyl,    C₃-C₈-cycloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the four    last mentioned aliphatic and cycloaliphatic radicals may be    partially or fully halogenated and/or may be substituted by one or    more radicals R⁸,    -   —Si(R¹²)₃, —OR⁹, —S(O)_(n)R⁹ and —NR^(10a)R^(10b);

-   R^(3a), R^(3b) are each independently selected from the group    consisting of hydrogen, halogen, hydroxyl, —CO₂R^(3d), C₁-C₃-alkyl,    C₁-C₃-haloalkyl, C₂-C₃-alkenyl, C₂-C₃-alkynyl, C₁-C₃-alkoxy,    C₁-C₃-haloalkoxy, C₁-C₃-alkylthio, C₁-C₃-haloalkylthio,    C₁-C₃-alkylsulfonyl and C₁-C₃-haloalkylsulfonyl; or R^(3a) and    R^(3b) together form a group ═O, ═C(R^(3c))₂, ═NOH or ═NOCH₃;

-   each R^(3c) is independently selected from the group consisting of    hydrogen, halogen, CH₃ and CF₃;

-   R^(3d) is selected from the group consisting of hydrogen,    C₁-C₆-alkyl and C₁-C₃-alkyloxy-C₁-C₃-alkyl-;

-   each R⁴ is independently selected from the group consisting of    hydrogen, halogen, cyano, azido, nitro, —SCN, —SF₅, C₁-C₆-alkyl    which may be partially or fully halogenated and/or may be    substituted by one or more radicals R⁸, C₃-C₈-cycloalkyl which may    be partially or fully halogenated and/or may be substituted by one    or more radicals R⁸, C₂-C₆-alkenyl which may be partially or fully    halogenated and/or may be substituted by one or more radicals R⁸,    C₂-C₆-alkynyl which may be partially or fully halogenated and/or may    be substituted by one or more radicals R⁸,    -   —Si(R¹²)₃, —OR⁹, —S(O)_(n)R⁹, and —NR^(10a)R^(10b);

-   each R⁵ is independently selected from the group consisting of    hydrogen, cyano, C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl,    C₂-C₁₀-alkynyl, wherein the four last-mentioned aliphatic and    cycloaliphatic radicals may be partially or fully halogenated and/or    may be substituted with one or more substituents R⁸; and    —S(O)_(n)R⁹,

-   each R⁶ is independently selected from the group consisting of    hydrogen, cyano, C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl,    C₂-C₁₀-alkynyl, wherein the four last-mentioned aliphatic and    cycloaliphatic radicals may be partially or fully halogenated and/or    may be substituted by one or more substituents R⁸, —OR⁹,    —NR^(10a)R^(10b), —S(O)_(n)R⁹, —C(═O)NR^(10a)N(R^(10a))R^(10b),    —Si(R¹²)₃, —C(═O)R⁸, —CH═NOR⁹,    -   phenyl which may be substituted with 1, 2, 3, 4, or 5        substituents R¹¹, and a 3-, 4-, 5-, 6-, 7-, 8-, 9- or        10-membered saturated, partially unsaturated or maximally        unsaturated heteromonocyclic or heterobicyclic ring containing        1, 2, 3 or 4 heteroatoms or heteroatom groups independently        selected from N, O, S, NO, SO and SO₂, as ring members, where        the heteromonocyclic or heterobicyclic ring may be substituted        with one or more substituents R¹¹;    -   or R⁵ and R⁶, together with the nitrogen atom to which they are        bound, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated,        partially unsaturated or maximally unsaturated heterocyclic        ring, where the ring may further contain 1, 2, 3 or 4        heteroatoms or heteroatom-containing groups selected from O, S,        N, SO, SO₂, C═O and C═S as ring members, wherein the        heterocyclic ring may be substituted with 1, 2, 3, 4 or 5        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,        C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,        C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl,        C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, wherein the        aliphatic or cycloaliphatic moieties in the twelve        last-mentioned radicals may be substituted by one or more        radicals R⁸, and phenyl which may be substituted with 1, 2, 3, 4        or 5 substituents R¹¹;    -   or R⁵ and R⁶ together form a group ═C(R⁸)₂, ═S(O)_(m)(R⁹)₂,        ═NR^(10a) or ═NOR⁹;    -   each R⁸ is independently selected from the group consisting of        cyano, azido, nitro, —SCN, —SF₅, C₃-C₈-cycloalkyl,        C₃-C₈-halocycloalkyl, where the cycloaliphatic moieties in the        two last-mentioned radicals may be substituted by one or more        radicals R¹³;    -   —Si(R¹²)₃, —OR⁹, —OSO₂R⁹, —S(O)_(n)R⁹, —N(R^(10a))R^(10b),        —C(═O)N(R^(10a))R^(10b), —C(═S)N(R^(10a))R^(10b), —C(═O)OR⁹,        —CH═NOR⁹,    -   phenyl, optionally substituted with 1, 2, 3, 4 or 5 substituents        R¹⁶, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially        unsaturated or maximally unsaturated heterocyclic ring        comprising 1, 2 or 3 heteroatoms or heteroatom groups selected        from N, O, S, NO, SO and SO₂, as ring members, where the        heterocyclic ring is optionally substituted with one or more        substituents R¹⁶, or    -   two R⁸ present on the same carbon atom of an alkyl, alkenyl,        alkynyl or cycloalkyl group together form a group ═O, ═C(R¹³)₂;        ═S; ═S(O)_(m)(R¹⁵)₂, ═S(O)_(m)R¹⁵N(R^(14a))R^(14b), ═NR^(10a),        ═NOR⁹; or ═NN(R^(10a))R^(10b);    -   or    -   two radicals R⁸, together with the carbon atoms of an alkyl,        alkenyl, alkynyl or cycloalkyl group which they are bonded to,        form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially        unsaturated carbocyclic or heterocyclic ring, where the        heterocyclic ring comprises 1, 2, 3 or 4 heteroatoms or        heteroatom groups independently selected from N, O, S, NO, SO        and SO₂, as ring members, and where the carbocyclic or        heterocyclic ring is optionally substituted with one or more        substituents R¹⁶; and    -   R⁸ as a substituent on a cycloalkyl ring is additionally        selected from the group consisting of C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl        and C₂-C₆-haloalkynyl, where the aliphatic moieties in these six        radicals may be substituted by one or more radicals R¹³; and    -   R⁸ in the groups —C(═O)R⁸ and ═C(R⁸)₂ is additionally selected        from the group consisting of hydrogen, halogen, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl        and C₂-C₆-haloalkynyl, where the aliphatic moieties in the six        last-mentioned radicals may be substituted by one or more        radicals R¹³;

-   each R⁹ is independently selected from the group consisting of    hydrogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl,    C₃-C₈-cycloalkyl-C₁-C₄-alkyl-, C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl,    C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, where the    aliphatic and cycloaliphatic moieties in the nine last-mentioned    radicals may be substituted by one or more radicals R¹³,    -   —C₁-C₆-alkyl-C(═O)OR¹⁵, —C₁-C₆-alkyl-C(═O)N(R^(14a))R^(14b),        —C₁-C₆-alkyl-C(═S)N(R^(14a))R^(14b),        —C₁-C₆-alkyl-C(═NR¹⁴)N(R^(14a))R^(14b), —Si(R¹²)₃, —S(O)_(n)R¹⁵,        —S(O)_(n)N(R^(14a))R^(14b), —N(R^(10a))R^(10b), —N═C(R¹³)₂,        —C(═O)R¹³, —C(═O)N(R^(14a))R^(14b), —C(═S)N(R^(14a))R^(14b),        —C(═O)OR¹⁵,    -   phenyl, optionally substituted with one or more substituents        R¹⁶; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially        unsaturated or maximally unsaturated heterocyclic ring        comprising 1, 2 or 3 heteroatoms or heteroatom groups selected        from N, O, S, NO, SO and SO₂, as ring members, where the        heterocyclic ring is optionally substituted with one or more        substituents R¹⁶; and R⁹ in the groups —S(O)_(n)R⁹ and —OSO₂R⁹        is additionally selected from the group consisting of        C₁-C₆-alkoxy and C₁-C₆-haloalkoxy;

-   R^(10a), R^(10b) are selected independently from one another from    the group consisting of hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,    C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl,    C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, where the    aliphatic and cycloaliphatic moieties in the eight last-mentioned    radicals may be substituted by one or more radicals R¹³;    -   —C₁-C₆-alkyl-C(═O)OR¹⁵, —C₁-C₆-alkyl-C(═O)N(R^(14a))R^(14b),        —C₁-C₆-alkyl-C(═S)N(R^(14a))R^(14b),        —C₁-C₆-alkyl-C(═NR¹⁴)N(R^(14a))R^(14b), C₁-C₆-alkoxy,        C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,    -   —S(O)_(n)R¹⁵, —S(O)_(n)N(R^(14a))R^(14b), —C(═O)R¹³, —C(═O)OR¹⁵,        —C(═O)N(R^(14a))R^(14b), —C(═S)R¹³, —C(═S)SR¹⁵,        —C(═S)N(R^(14a))R^(14b), —C(═NR¹⁴)R¹³;    -   phenyl, optionally substituted with 1, 2, 3, 4 or 5 substituents        R¹⁶; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially        unsaturated or maximally unsaturated heterocyclic ring        comprising 1, 2, 3 or 4 heteroatoms or heteroatom groups        selected from N, O, S, NO, SO and SO₂, as ring members, where        the heterocyclic ring is optionally substituted with one or more        substituents R¹⁶;    -   or    -   R^(10a) and R^(10b) form together with the nitrogen atom they        are bonded to a 3-, 4-, 5-, 6-, 7- or 8-membered saturated,        partially unsaturated or maximally unsaturated heterocyclic        ring, wherein the heterocyclic ring may additionally contain one        or two heteroatoms or heteroatom groups selected from N, O, S,        NO, SO and SO₂, as ring members, where the heterocyclic ring        optionally carries one or more substituents selected from        halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,        C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,        C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl,        C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, phenyl,        optionally substituted with 1, 2, 3, 4 or 5 substituents R¹⁶,        and a 3-, 4-, 5-, 6-, or 7-membered saturated, partially        unsaturated or maximally unsaturated heterocyclic ring        comprising 1, 2 or 3 heteroatoms or heteroatom groups selected        from N, O, S, NO, SO and SO₂, as ring members, where the        heterocyclic ring optionally carries one or more substituents        R¹⁶;    -   or R^(10a) and R^(10b) together form a group ═C(R¹³)₂,        ═S(O)_(m)(R¹⁵)₂, ═S(O)_(m)R¹⁵N(R^(14a))R^(14b), ═NR¹⁴ or ═NOR¹⁵;

-   R¹¹ is independently selected from the group consisting of halogen,    cyano, azido, nitro, —SCN, —SF₅, C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl,    C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, wherein the four last-mentioned    aliphatic and cycloaliphatic radicals may be partially or fully    halogenated and/or may be substituted with one or more radicals R⁸,    -   —OR⁹, —NR^(10a)R^(10b), —S(O)_(n)R⁹, —Si(R¹²)₃;    -   phenyl, optionally substituted with 1, 2, 3, 4, or 5        substituents selected independently from R¹⁶; and    -   a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated        or maximally unsaturated aromatic heterocyclic ring comprising        1, 2, 3 or 4 heteroatoms or heteroatom groups selected from N,        O, S, NO, SO and SO₂, as ring members, where the heterocyclic        ring is optionally substituted with one or more substituents        selected independently from R¹⁶;    -   or two R¹¹ present on the same ring carbon atom of an        unsaturated or partially unsaturated heterocyclic ring may        together form a group ═O, ═C(R¹³)₂; ═S; ═S(O)_(m)(R¹⁵)₂;        ═S(O)_(m)R¹⁵N(R^(14a))R^(14b), ═NR¹⁴, ═NOR¹⁵, or        ═NN(R^(14a))R^(14b);    -   or two R¹¹ present on the same S or SO ring member of a        heterocyclic ring may together form a group ═NR¹⁴, ═NOR¹⁵, or        ═NN(R^(14a))R^(14b);    -   or two R¹¹ bound on adjacent ring atoms form together with the        ring atoms to which they are bound a saturated 3-, 4-, 5-, 6-,        7-, 8- or 9-membered ring, wherein the ring may contain 1 or 2        heteroatoms or heteroatom groups selected from O, S, N, NR¹⁴,        NO, SO and SO₂ and/or 1 or 2 groups selected from C═O, C═S and        C═NR¹⁴ as ring members, and wherein the ring may be substituted        by one or more radicals selected from the group consisting of        halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,        C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,        C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl,        C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, phenyl        which may be substituted by 1, 2, 3, 4 or 5 radicals R¹⁶, and a        3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or        maximally unsaturated heterocyclic ring containing 1, 2 or 3        heteroatoms or heteroatom groups selected from N, O, S, NO, SO        and SO₂, as ring members, where the heterocyclic ring may be        substituted by one or more radicals R¹⁶;

-   each R¹² is independently selected from the group consisting of    hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,    C₁-C₆-haloalkoxy, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,    C₂-C₆-haloalkynyl, C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl,    C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-haloalkoxy-C₁-C₆-alkyl, and phenyl,    optionally substituted with 1, 2, 3, 4, or 5 substituents R¹⁶;

-   each R¹³ is independently selected from the group consisting of    cyano, nitro, —OH, —SH, —SCN, —SF₅, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,    C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,    C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,    C₁-C₆-haloalkylsulfonyl, trimethylsilyl, triethylsilyl,    tert-butyldimethylsilyl, —C(═O)N(R^(14a))R^(14b),    -   C₃-C₈-cycloalkyl which may be unsubstituted, partially or fully        halogenated and/or may carry 1 or 2 radicals selected from        C₁-C₄-alkyl, C₃-C₄-cycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy        and oxo; phenyl, benzyl, phenoxy, where the phenyl moiety in the        three last-mentioned radicals may be unsubstituted or carry 1,        2, 3, 4 or 5 substituents R¹⁶; and a 3-, 4-, 5-, 6- or        7-membered saturated, partially unsaturated or maximally        unsaturated heterocyclic ring containing 1, 2 or 3 heteroatoms        or heteroatom groups selected from N, O, S, NO, SO and SO₂, as        ring members, where the heterocyclic ring may be substituted by        1, 2 or 3 substituents R¹⁶;    -   or    -   two R¹³ present on the same carbon atom of an alkyl, alkenyl,        alkynyl or cycloalkyl group may together be ═O,        ═CH(C₁-C₄-alkyl), ═C(C₁-C₄-alkyl)C₁-C₄-alkyl, ═N(C₁-C₆-alkyl) or        ═NO(C₁-C₆-alkyl);    -   and    -   R¹³ as a substituent on a cycloalkyl ring is additionally        selected from the group consisting of C₁-C₆-alkyl, C₂-C₆-alkenyl        and C₂-C₆-alkynyl, wherein the three last-mentioned aliphatic        radicals may be unsubstituted, partially or fully halogenated        and/or may carry 1 or 2 substituents selected from CN,        C₃-C₄-cycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy and oxo;    -   and    -   R¹³ in the groups ═C(R¹³)₂, —N═C(R¹³)₂, —C(═O)R¹³, —C(═S)R¹³ and        —C(═NR¹⁴)R¹³ is additionally selected from the group consisting        of hydrogen, halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl and        C₂-C₆-alkynyl, wherein the three last-mentioned aliphatic        radicals may be unsubstituted, partially or fully halogenated        and/or may carry 1 or 2 radicals selected from CN,        C₃-C₄-cycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy and oxo;

-   each R¹⁴ is independently selected from the group consisting of    hydrogen, cyano, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,    C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl,    C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, trimethylsilyl,    triethylsilyl, tert-butyldimethylsilyl, C₁-C₆-alkyl, C₂-C₆-alkenyl,    C₂-C₆-alkynyl, wherein the three last-mentioned aliphatic radicals    may be unsubstituted, partially or fully halogenated and/or may    carry 1 or 2 radicals selected from CN, C₁-C₄-alkoxy,    C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl,    C₁-C₄-alkylsulfonyl, C₃-C₆-cycloalkyl which may be substituted by 1    or 2 substituents selected from halogen and cyano; and oxo;    C₃-C₈-cycloalkyl which may be unsubstituted, partially or fully    halogenated and/or may carry 1 or 2 radicals selected from cyano,    C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,    C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl, C₃-C₄-cycloalkyl,    C₃-C₄-cycloalkyl-C₁-C₄-alkyl-, where the cycloalkyl moiety in the    two last-mentioned radicals may be substituted by 1 or 2    substituents selected from halogen and cyano; and oxo;    -   phenyl, benzyl, pyridyl, phenoxy, wherein the cyclic moieties in        the four last-mentioned radicals may be unsubstituted and/or        carry 1, 2, 3 or 4 substituents selected from halogen, cyano,        nitro, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,        C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,        C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl,        C₂-C₄-haloalkynyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, and        (C₁-C₆-alkoxy)carbonyl; and a 3-, 4-, 5- or 6-membered        saturated, partially unsaturated or maximally unsaturated        heterocyclic ring comprising 1, 2 or 3 heteroatoms or heteroatom        groups selected from N, O, S, NO, SO and SO₂, as ring members,        where the heterocyclic ring is optionally substituted with one        or more substituents R¹⁶;

-   R^(14a) and R^(14b), independently of each other, have one of the    meanings given for R¹⁴;    -   or    -   R^(14a) and R^(14b), together with the nitrogen atom to which        they are bound, form a 3-, 4-, 5-, 6- or 7-membered saturated,        partially unsaturated or maximally unsaturated heterocyclic        ring, wherein the heterocyclic ring may additionally contain 1        or 2 heteroatoms or heteroatom groups selected from N, O, S, NO,        SO and SO₂, as ring members, where the heterocyclic ring        optionally carries one or more substituents selected from        halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and        C₁-C₄-haloalkoxy;    -   or    -   R^(14a) and R¹⁴ or R^(14b) and R¹⁴, together with the nitrogen        atoms to which they are bound in the group        —C(═NR¹⁴)N(R^(14a))R^(14b), form a 3-, 4-, 5-, 6- or 7-membered        partially unsaturated or maximally unsaturated heterocyclic        ring, wherein the heterocyclic ring may additionally contain 1        or 2 heteroatoms or heteroatom groups selected from N, O, S, NO,        SO and SO₂, as ring members, where the heterocyclic ring        optionally carries one or more substituents selected from        halogen, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;

-   each R¹⁵ is independently selected from the group consisting of    hydrogen, cyano, trimethylsilyl, triethylsilyl,    tert-butyldimethylsilyl,    -   C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the three        last-mentioned aliphatic radicals may be unsubstituted,        partially or fully halogenated and/or may carry 1 or 2 radicals        selected from C₃-C₄-cycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,        C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl and        oxo; C₃-C₈-cycloalkyl which may be unsubstituted, partially or        fully halogenated and/or may carry 1 or 2 radicals selected from        C₁-C₄-alkyl, C₃-C₄-cycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,        C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl and        oxo;    -   phenyl, benzyl, pyridyl and phenoxy, wherein the four        last-mentioned radicals may be unsubstituted, partially or fully        halogenated and/or carry 1, 2 or 3 substituents selected from        C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy and        (C₁-C₆-alkoxy)carbonyl;

-   each R¹⁶ is independently selected from the group consisting of    halogen, nitro, cyano, —OH, —SH, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,    C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,    C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,    C₁-C₆-haloalkylsulfonyl, C₁-C₄-alkylcarbonyl,    C₁-C₄-haloalkylcarbonyl, C₁-C₄-alkoxycarbonyl,    C₁-C₄-haloalkoxycarbonyl, aminocarbonyl, C₁-C₄-alkylaminocarbonyl,    di-(C₁-C₄-alkyl)-aminocarbonyl, trimethylsilyl, triethylsilyl,    tert-butyldimethylsilyl;    -   C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the three        last-mentioned aliphatic radicals may be unsubstituted,        partially or fully halogenated and/or may carry 1 or 2 radicals        selected from cyano, C₃-C₄-cycloalkyl, C₁-C₄-alkoxy,        C₁-C₄-haloalkoxy and oxo;    -   C₃-C₈-cycloalkyl which may be unsubstituted, partially or fully        halogenated and/or may carry 1 or 2 radicals selected from        cyano, C₁-C₄-alkyl, C₃-C₄-cycloalkyl, C₁-C₄-alkoxy,        C₁-C₄-haloalkoxy and oxo;    -   phenyl, benzyl, pyridyl and phenoxy, wherein the four last        mentioned radicals may be unsubstituted, partially or fully        halogenated and/or carry 1, 2 or 3 substituents selected from        C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy and        (C₁-C₆-alkoxy)carbonyl;    -   or    -   two R¹⁶ present together on the same atom of an unsaturated or        partially unsaturated ring may be ═O, ═S, ═N(C₁-C₆-alkyl),        ═NO(C₁-C₆-alkyl), ═CH(C₁-C₄-alkyl) or        ═C(C₁-C₄-alkyl)C₁-C₄-alkyl; or    -   or two R¹⁶ present on the same S or SO ring member of a        heterocyclic ring may together form a group ═N(C₁-C₆-alkyl),        ═NO(C₁-C₆-alkyl), ═NN(H)(C₁-C₆-alkyl) or ═NN(C₁-C₆-alkyl)₂;    -   or    -   two R¹⁶ on two adjacent carbon atoms form together with the        carbon atoms they are bonded to a 4-, 5-, 6-, 7- or 8-membered        saturated, partially unsaturated or maximally unsaturated ring,        wherein the ring may contain 1 or 2 heteroatoms or heteroatom        groups selected from N, O, S, NO, SO and SO₂, as ring members,        and wherein the ring optionally carries one or more substituents        selected from halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,        C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;

-   each n is independently 0, 1 or 2; and

-   each m is independently 0 or 1;    and the N-oxides, stereoisomers and agriculturally or veterinarily    acceptable salts thereof.

Preferably, however, the invention relates to compounds of formula I

wherein

-   X¹ is O or CH₂;-   A is a group of following formula:

-   -   wherein    -   # denotes the bond to the aromatic ring of formula (I);    -   W is selected from O and S;    -   Y is selected from hydrogen, —N(R⁵)R⁶ and —OR⁹;

-   B¹, B² and B³ are each independently CR²;

-   G¹ and G² are each independently CR⁴;

-   R^(g1) and R^(g2) form together a bridging group selected from    —CH₂CH₂CH₂CH₂— and —CH₂CH₂CH₂—;

-   R¹ is CF₃;

-   each R² is independently selected from the group consisting of    hydrogen, halogen, C₁-C₂-haloalkoxy and C₁-C₂-haloalkyl;

-   R^(3a), R^(3b) are each independently selected from the group    consisting of hydrogen, halogen, hydroxyl, —CO₂R^(3d), C₁-C₃-alkyl,    C₁-C₃-haloalkyl, C₂-C₃-alkenyl, C₂-C₃-alkynyl, C₁-C₃-alkoxy,    C₁-C₃-haloalkoxy, C₁-C₃-alkylthio, C₁-C₃-haloalkylthio,    C₁-C₃-alkylsulfonyl and C₁-C₃-haloalkylsulfonyl; or

-   R^(3a) and R^(3b) together form a group ═O, ═C(R^(3c))₂, ═NOH or    ═NOCH₃;

-   each R^(3c) is independently selected from the group consisting of    hydrogen, halogen, CH₃ and CF₃;

-   R^(3d) is selected from the group consisting of hydrogen,    C₁-C₆-alkyl and C₁-C₃-alkyloxy-C₁-C₃-alkyl-;

-   each R⁴ is independently selected from the group consisting of    hydrogen, halogen and cyano;

-   R⁵ selected from hydrogen, C₁-C₆-alkyl, C₂-C₃-alkynyl and CH₂—CN;

-   R⁶ is selected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,    C₁-C₄-alkyl which carries one radical R⁸, C₂-C₆-alkenyl,    C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl which may be    substituted by 1 or 2 substituents selected from F, CN and pyridyl;    —N(R^(101a))R^(101b),    -   wherein    -   R^(101a) is selected from hydrogen and C₁-C₆-alkyl; and    -   R^(101b) is selected from hydrogen, —C(═O)N(R^(14a))R^(14b),        wherein        -   R^(14a) is selected from the group consisting of hydrogen            and C₁-C₆-alkyl; and        -   R^(101b) is selected from the group consisting of hydrogen,            C₁-C₆-alkyl, C₂-C₄-alkynyl, CH₂—CN, C₁-C₆-haloalkyl,            C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₁-C₄-alkoxy and            C₁-C₄-haloalkoxy;        -   R^(101b) is further selected from phenyl, optionally            substituted with 1, 2, 3, 4 or 5 substituents R¹⁶, and a            heterocyclic ring selected from rings of formulae E-1 to            E-42

-   -   -   -   where in these rings E-1 to E-42 as a meaning for                R^(101b)            -   the zigzag line denotes the attachment point to the                remainder of the molecule;            -   k is 0, 1, 2 or 3, and            -   each R¹⁶ is independently selected from the group                consisting of halogen, cyano, nitro, C₁-C₄-alkyl,                C₁-C₄-haloalkyl, C₁—C₄-alkoxy, C₁-C₄-haloalkoxy,                C₁-C₄-alkylthio, C₁-C₄-haloalkylthio,                C₁-C₄-alkylsulfinyl, C₁-C₄-haloalkylsulfinyl,                C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl,                C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl,                C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl,                C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl,                aminocarbonyl, C₁-C₄-alkylaminocarbonyl and                di-(C₁-C₄-alkyl)aminocarbonyl;

    -   R⁶ is further selected from —CH═NOR^(9a), wherein R^(9a) is        selected from hydrogen, C₁-C₆-alkyl and C₁-C₆-haloalkyl;

    -   phenyl which may be substituted with 1, 2, 3, 4, or 5        substituents R¹¹, and a 3-, 4-, 5- or 6-membered saturated,        partially unsaturated or maximally unsaturated heteromonocyclic        ring containing 1, 2 or 3 heteroatoms or heteroatom groups        independently selected from N, O, S, NO, SO and SO₂, as ring        members, where the heteromonocyclic ring may be substituted with        one or more substituents R¹¹; wherein

    -   each R¹¹ is independently selected from the group consisting of        halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl,        C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,        C₁-C₄-haloalkylthio, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,        C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl and        C₂-C₄-haloalkynyl; or two R¹¹ present on the same carbon atom of        a saturated heterocyclic ring may form together ═O or ═S; or two        R¹¹ present on the same S or SO ring member of a heterocyclic        ring may together form a group ═N(C₁-C₆-alkyl),        ═NO(C₁-C₆-alkyl), ═NN(H)(C₁-C₆-alkyl) or ═NN(C₁-C₆-alkyl)₂;

    -   each R⁸ is independently selected from OH, CN, C₃-C₈-cycloalkyl        which optionally carries a CN or a C₁-C₂-haloalkyl substituent;        C₃-C₈-halocycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfonyl,        C₁-C₆-haloalkylsulfonyl, —C(═O)N(R^(102a))R^(102b), phenyl,        optionally substituted with 1, 2, 3, 4 or 5 substituents R¹⁶,        and a 3-, 4-, 5- or 6-membered saturated, partially unsaturated        or maximally unsaturated heteromonocyclic ring containing 1, 2,        3 or 4 heteroatoms or heteroatom groups independently selected        from N, O, S, NO, SO and SO₂, as ring members, where the        heteromonocyclic ring may be substituted with one or more        substituents R¹⁶;        -   wherein        -   R^(102a) is selected from the group consisting of hydrogen,            C₁-C₆-alkyl, C₂-C₃-alkynyl and CH₂—CN;        -   R^(102b) is selected from the group consisting of hydrogen,            C₁-C₆-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, CH₂—CN,            C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,            C₃-C₆-cycloalkylmethyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,            phenyl which is optionally substituted with 1, 2, 3, 4 or 5            substituents selected from the group consisting of halogen,            cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl,            C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl,            C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₁-C₄-alkoxy,            C₁-C₄-haloalkoxy, C₁-C₄-alkylthio and C₁-C₄-haloalkylthio;            and a heterocyclic ring selected from rings of formulae E-1            to E-42 as defined above and E-43 to E-57:

-   -   -   -   where in these rings E-43 to E-57 the zigzag line                denotes the attachment point to the remainder of the                molecule;            -   k is 0, 1, 2 or 3,            -   n is 0, 1 or 2; and            -   each R¹⁶ is independently selected from the group                consisting of halogen, cyano, nitro, C₁-C₄-alkyl,                C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,                C₁-C₄-alkylthio, C₁-C₄-haloalkylthio,                C₁-C₄-alkylsulfinyl, C₁-C₄-haloalkylsulfinyl,                C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl,                C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl,                C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl,                C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl,                aminocarbonyl, C₁-C₄-alkylaminocarbonyl and                di-(C₁-C₄-alkyl)aminocarbonyl; or            -   two R¹⁶ present on the same carbon atom of a saturated                ring may form together ═O or ═S; and

        -   each R¹⁶ as a substituent on phenyl (as a meaning of R⁸) or            the heterocyclic rings (as a meaning of R⁸) is independently            selected from the group consisting of halogen, cyano, nitro,            C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,            C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio,            C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl,            C₂-C₄-haloalkenyl, C₂-C₄-alkynyl and C₂-C₄-haloalkynyl; or            -   two R¹⁶ present on the same carbon atom of a saturated                heterocyclic ring may form together ═O or ═S; or            -   two R¹⁶ present on the same S or SO ring member of a                heterocyclic ring may together form a group                ═N(C₁-C₆-alkyl), ═NO(C₁-C₆-alkyl), ═NN(H)(C₁-C₆-alkyl)                or ═NN(C₁-C₆-alkyl)₂;

-   or

-   R⁵ and R⁶, together with the nitrogen atom to which they are bound,    form a 5- or 6-membered saturated heterocyclic ring, where the ring    may further contain 1 or 2 heteroatoms or heteroatom-containing    groups selected from O, S, SO, SO₂, NH and C═O as ring members,    wherein the heterocyclic ring may be substituted with 1, 2 or 3    substituents independently selected from the group consisting of    halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and    C₁-C₆-haloalkoxy;

-   or

-   R⁵ and R⁶ together form a group ═S(R^(9b))₂, where R^(9b) is    selected from C₁-C₆-alkyl and C₁-C₆-haloalkyl;

-   R⁹ is selected from the group consisting of hydrogen, C₁-C₆-alkyl,    C₁-C₆-haloalkyl and C₁-C₆-alkyl substituted by one radical R¹³;    where R¹³ is selected from CN, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,    C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,    C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,    C₁-C₆-haloalkylsulfonyl and a heterocyclic ring selected from rings    of formulae E-1 to E-57 as defined above;    -   where in these rings E-1 to E-57 as a meaning of R¹³ the zigzag        line denotes the attachment point to the remainder of the        molecule;    -   k is 0, 1, 2 or 3,    -   n is 0, 1 or 2; and    -   each R¹⁶ is independently selected from the group consisting of        halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl,        C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,        C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfinyl,        C₁-C₄-haloalkylsulfinyl, C₁-C₄-alkylsulfonyl,        C₁-C₄-haloalkylsulfonyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,        C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl,        C₂-C₄-haloalkynyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl,        aminocarbonyl, C₁-C₄-alkylaminocarbonyl and        di-(C₁-C₄-alkyl)aminocarbonyl; or        -   two R¹⁶ present on the same carbon atom of a saturated ring            may form together ═O or ═S; and

-   each R¹⁶ in all other cases (i.e. as a substituent on phenyl as a    meaning for R^(101b)) is independently selected from the group    consisting of halogen, nitro, cyano, —OH, —SH, C₁-C₆-alkoxy,    C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,    C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,    C₁-C₆-haloalkylsulfonyl, C₁-C₄-alkylcarbonyl,    C₁-C₄-haloalkylcarbonyl, C₁-C₄-alkoxycarbonyl,    C₁-C₄-haloalkoxycarbonyl, aminocarbonyl, C₁-C₄-alkylaminocarbonyl,    di-(C₁-C₄-alkyl)-aminocarbonyl, trimethylsilyl, triethylsilyl,    tert-butyldimethylsilyl;    -   C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the three        last-mentioned aliphatic radicals may be unsubstituted,        partially or fully halogenated and/or may carry 1 or 2 radicals        selected from cyano, C₃-C₄-cycloalkyl, C₁-C₄-alkoxy,        C₁-C₄-haloalkoxy and oxo;    -   C₃-C₈-cycloalkyl which may be unsubstituted, partially or fully        halogenated and/or may carry 1 or 2 radicals selected from        cyano, C₁-C₄-alkyl, C₃-C₄-cycloalkyl, C₁-C₄-alkoxy,        C₁-C₄-haloalkoxy and oxo;    -   phenyl, benzyl, pyridyl and phenoxy, wherein the four last        mentioned radicals may be unsubstituted, partially or fully        halogenated and/or carry 1, 2 or 3 substituents selected from        C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy and        (C₁-C₆-alkoxy)carbonyl;    -   or    -   two R¹⁶ present together on the same atom of an unsaturated or        partially unsaturated ring may be ═O, ═S, ═N(C₁-C₆-alkyl),        ═NO(C₁-C₆-alkyl), ═CH(C₁-C₄-alkyl) or        ═C(C₁-C₄-alkyl)C₁-C₄-alkyl; or    -   or two R¹⁶ present on the same S or SO ring member of a        heterocyclic ring may together form a group ═N(C₁-C₆-alkyl),        ═NO(C₁-C₆-alkyl), ═NN(H)(C₁-C₆-alkyl) or ═NN(C₁-C₆-alkyl)₂;    -   or    -   two R¹⁶ on two adjacent carbon atoms form together with the        carbon atoms they are bonded to a 4-, 5-, 6-, 7- or 8-membered        saturated, partially unsaturated or maximally unsaturated ring,        wherein the ring may contain 1 or 2 heteroatoms or heteroatom        groups selected from N, O, S, NO, SO and SO₂, as ring members,        and wherein the ring optionally carries one or more substituents        selected from halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,        C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;        and the N-oxides, stereoisomers and agriculturally or        veterinarily acceptable salts thereof.

In a particular embodiment, R¹¹, in addition to the above definitions,is further selected from C₃-C₆-cycloalkyl-C₁-C₄-alkyl.

In a particular embodiment, the invention relates to compounds I asdefined in the above preferred embodiment, the N-oxides, stereoisomersand agriculturally or veterinarily acceptable salts thereof, wherehowever

-   each R⁸ is independently selected from OH, CN, C₃-C₈-cycloalkyl    which optionally carries a CN or CF₃ substituent,    C₃-C₈-halocycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,    C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfonyl,    C₁-C₆-haloalkylsulfonyl, —C(═O)N(R^(102a))R^(102b), phenyl,    optionally substituted with 1, 2, 3, 4 or 5 substituents R¹⁶, and a    3-, 4-, 5- or 6-membered saturated, partially unsaturated or    maximally unsaturated heteromonocyclic ring containing 1, 2 or 3    heteroatoms or heteroatom groups independently selected from N, O,    S, NO, SO and SO₂, as ring members, where the heteromonocyclic ring    may be substituted with one or more substituents R¹⁶;    -   wherein    -   R^(102a) is selected from the group consisting of hydrogen,        C₁-C₆-alkyl, C₂-C₃-alkynyl and CH₂—CN;    -   R^(102b) is selected from the group consisting of hydrogen,        C₁-C₆-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, CH₂—CN,        C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,        C₃-C₆-cycloalkylmethyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, phenyl        which is optionally substituted with 1, 2, 3, 4 or 5        substituents selected from the group consisting of halogen,        cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl,        C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl,        C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₁-C₄-alkoxy,        C₁-C₄-haloalkoxy, C₁-C₄-alkylthio and C₁-C₄-haloalkylthio; and a        heterocyclic ring selected from rings of formulae E-1 to E-42 as        defined above and E-43 to E-57:

-   -   -   where in these rings E-43 to E-57        -   the zigzag line denotes the attachment point to the            remainder of the molecule;        -   k is 0, 1, 2 or 3,        -   n is 0, 1 or 2; and        -   each R¹⁶ is independently selected from the group consisting            of halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl,            C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,            C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfinyl,            C₁-C₄-haloalkylsulfinyl, C₁-C₄-alkylsulfonyl,            C₁-C₄-haloalkylsulfonyl, C₃-C₆-cycloalkyl,            C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl,            C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C₁-C₄-alkylcarbonyl,            C₁-C₄-haloalkylcarbonyl, aminocarbonyl,            C₁-C₄-alkylaminocarbonyl and di-(C₁-C₄-alkyl)aminocarbonyl;            or            -   two R¹⁶ present on the same carbon atom of a saturated                ring may form together ═O or ═S; and

    -   each R¹⁶ as a substituent on phenyl (as a meaning of R⁸) or the        heterocyclic rings (as a meaning of R⁸) is independently        selected from the group consisting of halogen, cyano, nitro,        C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,        C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₃-C₆-cycloalkyl,        C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl,        C₂-C₄-alkynyl and C₂-C₄-haloalkynyl; or        -   two R¹⁶ present on the same carbon atom of a saturated            heterocyclic ring may form together ═O or ═S; or        -   two R¹⁶ present on the same S or SO ring member of a            heterocyclic ring may together form a group ═N(C₁-C₆-alkyl),            ═NO(C₁-C₆-alkyl), ═NN(H)(C₁-C₆-alkyl) or ═NN(C₁-C₆-alkyl)₂.

The present invention also provides an agricultural compositioncomprising at least one compound of the formula I as defined herein, astereoisomer thereof and/or at least one agriculturally acceptable saltthereof and at least one inert liquid and/or solid agriculturallyacceptable carrier.

The present invention also provides a veterinary composition comprisingat least one compound of the formula I as defined herein, a stereoisomerthereof and/or at least one veterinarily acceptable salt thereof and atleast one inert liquid and/or solid veterinarily acceptable carrier.

The present invention also provides a method for controllinginvertebrate pests which method comprises treating the pests, their foodsupply, their habitat or their breeding ground or a cultivated plant,plant propagation materials (such as seed), soil, area, material orenvironment in which the pests are growing or may grow, or thematerials, cultivated plants, plant propagation materials (such asseed), soils, surfaces or spaces to be protected from pest attack orinfestation with a pesticidally effective amount of a compound offormula I, a stereoisomer thereof and/or at least one agriculturallyacceptable salt thereof as defined herein.

The method serves in particular for protecting plants from attack orinfestation by invertebrate pests, and thus comprises treating theplants with a pesticidally effective amount of at least one compound ofthe formula I as defined above, a stereoisomer thereof and/or at leastone agriculturally acceptable salt thereof. The method further serves inparticular for protecting plant propagation material and/or the plantswhich grow therefrom from attack or infestation by invertebrate pests,and thus comprises treating the plant propagation material with apesticidally effective amount of at least one compound of the formula Ias defined above, a stereoisomer thereof and/or at least oneagriculturally acceptable salt thereof.

The present invention also relates to plant propagation material, inparticular seed, comprising at least one compound of formula I, astereoisomer thereof and/or at least one agriculturally acceptable saltthereof as defined herein.

The present invention further relates to a method for treating orprotecting an animal from infestation or infection by parasites(invertebrate pests) which comprises bringing the animal in contact witha parasiticidally/pesticidally effective amount of a compound of theformula I, a stereoisomer thereof and/or at least one veterinarilyacceptable salt thereof as defined herein. Bringing the animal incontact with the compound I, its salt or the veterinary composition ofthe invention means applying or administering it to the animal.

The present invention further relates to compounds of the formula I,stereoisomers thereof and/or veterinarily acceptable salts thereof asdefined herein for use as a medicament, especially for use as amedicament for treating or protecting an animal from infestation orinfection by parasites (invertebrate pests).

The term “steroisomers” encompasses both optical isomers, such asenantiomers or diastereomers, the latter existing due to more than onecenter of chirality in the molecule, as well as geometrical isomers(cis/trans isomers).

Depending on the substitution pattern, the compounds of the formula Imay have one or more centers of chirality, in which case they arepresent as mixtures of enantiomers or diastereomers. One center ofchirality is the carbon ring atom of the isoxazoline or pyrroline ringcarrying radical R¹. The invention provides both the pure enantiomers ordiastereomers and their mixtures and the use according to the inventionof the pure enantiomers or diastereomers of the compound I or itsmixtures. Suitable compounds of the formula I also include all possiblegeometrical stereoisomers (cis/trans isomers) and mixtures thereof.

In a specific embodiment, the compounds I are present in form of amixture of compounds I.1 and I.2

where compound I.1 is present in an amount of more than 50% by weight,in particular of at least 70% by weight, specifically of at least 90% byweight, based on the total weight of compounds I.1 and I.2.

The term N-oxides relates to a form of compounds I in which at least onenitrogen atom is present in oxidized form (as NO). To be more precise,it relates to any compound of the present invention which has at leastone tertiary nitrogen atom that is oxidized to an N-oxide moiety.N-oxides of compounds I can in particular be prepared by oxidizing e.g.the ring nitrogen atom of the isoxazoline/pyrroline moiety and/or, if G¹or G² is N, this nitrogen atom, and/or of the bridging group formed byR^(g1) and R^(g2) and/or of any nitrogen-containing heterocyclic grouppresent in group A with a suitable oxidizing agent, such as peroxocarboxylic acids or other peroxides. The person skilled in the art knowsif and in which positions compounds of the present invention may formN-oxides.

The compounds of the present invention may be amorphous or may exist inone ore more different crystalline states (polymorphs) which may have adifferent macroscopic properties such as stability or show differentbiological properties such as activities. The present invention includesboth amorphous and crystalline compounds of the formula I, mixtures ofdifferent crystalline states of the respective compound I, as well asamorphous or crystalline salts thereof.

Salts of the compounds of the formula I are preferably agriculturallyand veterinarily acceptable salts. They can be formed in a customarymethod, e.g. by reacting the compound with an acid of the anion inquestion if the compound of formula I has a basic functionality or byreacting an acidic compound of formula I with a suitable base.

Suitable agriculturally acceptable salts are especially the salts ofthose cations or the acid addition salts of those acids whose cationsand anions, respectively, do not have any adverse effect on the actionof the compounds according to the present invention. Suitable cationsare in particular the ions of the alkali metals, preferably lithium,sodium and potassium, of the alkaline earth metals, preferably calcium,magnesium and barium, and of the transition metals, preferablymanganese, copper, zinc and iron, and also ammonium (NH⁴⁺) andsubstituted ammonium in which one to four of the hydrogen atoms arereplaced by C₁-C₄-alkyl, C₁-C₄-hydroxyalkyl, C₁-C₄-alkoxy,C₁-C₄-alkoxy-C₁-C₄-alkyl, hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl orbenzyl. Examples of substituted ammonium ions comprise methylammonium,isopropylammonium, dimethylammonium, diisopropylammonium,trimethylammonium, tetramethylammonium, tetraethylammonium,tetrabutylammonium, 2-hydroxyethylammonium,2-(2-hydroxyethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium,benzyltrimethylammonium and benzl-triethylammonium, furthermorephosphonium ions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium,and sulfoxonium ions, preferably tri(C₁-C₄-alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide,fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogenphosphate, phosphate, nitrate, hydrogen carbonate, carbonate,hexafluorosilicate, hexafluorophosphate, benzoate, and the anions ofC₁-C₄-alkanoic acids, preferably formate, acetate, propionate andbutyrate. They can be formed by reacting a compound of formulae I withan acid of the corresponding anion, preferably of hydrochloric acid,hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

By the term “veterinarily acceptable salts” is meant salts of thosecations or anions which are known and accepted in the art for theformation of salts for veterinary use. Suitable acid addition salts,e.g. formed by compounds of formula I containing a basic nitrogen atom,e.g. an amino group, include salts with inorganic acids, for examplehydrochlorids, sulphates, phosphates, and nitrates and salts of organicacids for example acetic acid, maleic acid, dimaleic acid, fumaric acid,difumaric acid, methane sulfenic acid, methane sulfonic acid, andsuccinic acid.

The term “invertebrate pest” as used herein encompasses animalpopulations, such as insects, arachnids and nematodes, which may attackplants, thereby causing substantial damage to the plants attacked, aswell as ectoparasites which may infest animals, in particular warmblooded animals such as e.g. mammals or birds, or other higher animalssuch as reptiles, amphibians or fish, thereby causing substantial damageto the animals infested.

The term “plant propagation material” is to be understood to denote allthe generative parts of the plant such as seeds and vegetative plantmaterial such as cuttings and tubers (e. g. potatoes), which can be usedfor the multiplication of the plant. This includes seeds, roots, fruits,tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants,including seedlings and young plants, which are to be transplanted aftergermination or after emergence from soil. The plant propagationmaterials may be treated prophylactically with a plant protectioncompound either at or before planting or transplanting. Said youngplants may also be protected before transplantation by a total orpartial treatment by immersion or pouring.

The term “plants” comprises any types of plants including“non-cultivated plants” and in particular “cultivated plants”.

The term “non-cultivated plants” refers to any wild type species orrelated species or related genera of a cultivated plant.

The term “cultivated plants” is to be understood as including plantswhich have been modified by breeding, mutagenesis or genetic engineeringincluding but not limiting to agricultural biotech products on themarket or in development (cf.http://www.bio.org/speeches/pubs/er/agri_products.asp). Geneticallymodified plants are plants, which genetic material has been so modifiedby the use of recombinant DNA techniques that under naturalcircumstances cannot readily be obtained by cross breeding, mutations ornatural recombination. Typically, one or more genes have been integratedinto the genetic material of a genetically modified plant in order toimprove certain properties of the plant. Such genetic modifications alsoinclude but are not limited to targeted post-translational modificationof protein(s), oligo- or polypeptides e. g. by glycosylation or polymeradditions such as prenylated, acetylated or farnesylated moieties or PEGmoieties.

Plants that have been modified by breeding, mutagenesis or geneticengineering, e. g. have been rendered tolerant to applications ofspecific classes of herbicides, such as auxin herbicides such as dicambaor 2,4-D; bleacher herbicides such as hydroxyl-phenylpyruvatedioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibit-tors;acetolactate synthase (ALS) inhibitors such as sulfonyl ureas orimidazolinones; enolpyruvylshikimate-3-phosphate synthase (EPSPS)inhibitors, such as glyphosate; glutamine synthetase (GS) inhibitorssuch as glufosinate; protoporphyrinogen-IX oxidase inhibitors; lipidbiosynthesis inhibitors such as acetyl CoA carboxylase (ACCase)inhibitors; or oxynil (i. e. bromoxynil or ioxynil) herbicides as aresult of conventional methods of breeding or genetic engineering.Furthermore, plants have been made resistant to multiple classes ofherbicides through multiple genetic modifications, such as resistance toboth glyphosate and glufosinate or to both glyphosate and a herbicidefrom another class such as ALS inhibitors, HPPD inhibitors, auxinherbicides, or ACCase inhibitors. These herbicide resistancetechnologies are e. g. described in Pest Managem. Sci. 61, 2005, 246;61, 2005, 258; 61, 2005, 277; 61, 2005, 269; 61, 2005, 286; 64, 2008,326; 64, 2008, 332; Weed Sci. 57, 2009, 108; Austral. J. Agricult. Res.58, 2007, 708; Science 316, 2007, 1185; and references quoted therein.Several cultivated plants have been rendered tolerant to herbicides byconventional methods of breeding (mutagenesis), e. g. Clearfield® summerrape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e. g.imazamox, or ExpressSun® sunflowers (DuPont, USA) being tolerant tosulfonyl ureas, e. g. tribenuron. Genetic engineering methods have beenused to render cultivated plants such as soybean, cotton, corn, beetsand rape, tolerant to herbicides such as glyphosate and glufosinate,some of which are commercially available under the trade namesRoundupReady® (glyphosate-tolerant, Monsanto, U.S.A.), Cultivance®(imidazolinone tolerant, BASF SE, Germany) and LibertyLink®(glufosinate-tolerant, Bayer CropScience, Germany).

Furthermore, plants are also covered that are by the use of recombinantDNA techniques capable to synthesize one or more insecticidal proteins,especially those known from the bacterial genus Bacillus, particularlyfrom Bacillus thuringiensis, such as δ-endotoxins, e. g. CryIA(b),CryIA(c), CrIIF, CrIIF(a2), CryIIA(b), CryIIIA, CryIIIB(b1) or Cry9c;vegetative insecticidal proteins (VIP), e. g. VIP1, VIP2, VIP3 or VIP3A;insecticidal proteins of bacteria colonizing nematodes, e. g.Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, suchas scorpion toxins, arachnid toxins, wasp toxins, or otherinsect-specific neurotoxins; toxins produced by fungi, suchStreptomycetes toxins, plant lectins, such as pea or barley lectins;agglutinins; proteinase inhibitors, such as trypsin inhibitors, serineprotease inhibitors, patatin, cystatin or papain inhibitors;ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin,luffin, saporin or bryodin; steroid metabolism enzymes, such as3-hydroxy-steroid oxidase, ecdysteroid-IDP-glycosyl-transferase,cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ionchannel blockers, such as blockers of sodium or calcium channels;juvenile hormone esterase; diuretic hormone receptors (helicokininreceptors); stilben synthase, bibenzyl synthase, chitinases orglucanases. In the context of the present invention these insecticidalproteins or toxins are to be understood expressly also as pre-toxins,hybrid proteins, truncated or otherwise modified proteins. Hybridproteins are characterized by a new combination of protein domains,(see, e. g. WO 02/015701). Further examples of such toxins orgenetically modified plants capable of synthesizing such toxins aredisclosed, e. g., in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427529, EP-A 451 878, WO 03/18810 and WO 03/52073. The methods forproducing such genetically modified plants are generally known to theperson skilled in the art and are described, e. g. in the publicationsmentioned above. These insecticidal proteins contained in thegenetically modified plants impart to the plants producing theseproteins tolerance to harmful pests from all taxonomic groups ofathropods, especially to beetles (Coeloptera), two-winged insects(Diptera), and moths (Lepidoptera) and to nematodes (Nematoda).Genetically modified plants capable to synthesize one or moreinsecticidal proteins are, e. g., described in the publicationsmentioned above, and some of which are commercially available such asYieldGard® (corn cultivars producing the CrylAb toxin), YieldGard® Plus(corn cultivars producing CrylAb and Cry3Bb1 toxins), Starlink® (corncultivars producing the Cry9c toxin), Herculex® RW (corn cultivarsproducing Cry34Ab1, Cry35Ab1 and the enzymePhosphinothricin-N-Acetyltransferase [PAT]); NuCOTN® 33B (cottoncultivars producing the Cry1Ac toxin), Bollgard® I (cotton cultivarsproducing the Cry1Ac toxin), Bollgard® II (cotton cultivars producingCry1Ac and Cry2Ab2 toxins); VIPCOT® (cotton cultivars producing aVIP-toxin); NewLeaf® (potato cultivars producing the Cry3A toxin);Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt11 (e. g.Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France, (corn cultivarsproducing the Cry1Ab toxin and PAT enyzme), MIR604 from Syngenta SeedsSAS, France (corn cultivars producing a modified version of the Cry3Atoxin, c.f. WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium(corn cultivars producing the Cry3Bb1 toxin), IPC 531 from MonsantoEurope S.A., Belgium (cotton cultivars producing a modified version ofthe Cry1Ac toxin) and 1507 from Pioneer Overseas Corporation, Belgium(corn cultivars producing the Cry1F toxin and PAT enzyme).

Furthermore, plants are also covered that are by the use of recombinantDNA techniques capable to synthesize one or more proteins to increasethe resistance or tolerance of those plants to bacterial, viral orfungal pathogens. Examples of such proteins are the so-called“pathogenesis-related proteins” (PR proteins, see, e. g. EP-A 392 225),plant disease resistance genes (e. g. potato cultivars, which expressresistance genes acting against Phytophthora infestans derived from themexican wild potato Solanum bulbocastanum) or T4-lysozym (e. g. potatocultivars capable of synthesizing these proteins with increasedresistance against bacteria such as Erwinia amylvora). The methods forproducing such genetically modified plants are generally known to theperson skilled in the art and are described, e. g. in the publicationsmentioned above.

Furthermore, plants are also covered that are by the use of recombinantDNA techniques capable to synthesize one or more proteins to increasethe productivity (e. g. bio mass production, grain yield, starchcontent, oil content or protein content), tolerance to drought, salinityor other growth-limiting environmental factors or tolerance to pests andfungal, bacterial or viral pathogens of those plants.

Furthermore, plants are also covered that contain by the use ofrecombinant DNA techniques a modified amount of substances of content ornew substances of content, specifically to improve human or animalnutrition, e. g. oil crops that produce health-promoting long-chainomega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera®rape, DOW Agro Sciences, Canada).

Furthermore, plants are also covered that contain by the use ofrecombinant DNA techniques a modified amount of substances of content ornew substances of content, specifically to improve raw materialproduction, e. g. potatoes that produce increased amounts of amylopectin(e. g. Amflora® potato, BASF SE, Germany).

The organic moieties mentioned in the above definitions of the variablesare—like the term halogen—collective terms for individual listings ofthe individual group members. The prefix C_(n)-C_(m) indicates in eachcase the possible number of carbon atoms in the group.

The term halogen denotes in each case fluorine, bromine, chlorine oriodine, in particular fluorine, chlorine or bromine.

The term “alkyl” as used herein and in the alkyl moieties of alkoxy,alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyland the like refers to saturated straight-chain or branched hydrocarbonradicals having 1 to 2 (“C₁-C₂-alkyl”), 1 to 3 (“C₁-C₃-alkyl”), 1 to 4(“C₁-C₄-alkyl”), 1 to 6 (“C₁-C₆-alkyl”), 1 to 8 (“C₁-C₈-alkyl”) or 1 to10 (“C₁-C₁₀-alkyl”) carbon atoms. C₁-C₂-Alkyl is methyl or ethyl.C₁-C₃-Alkyl is additionally propyl and isopropyl. C₁-C₄-Alkyl isadditionally n-butyl, 1-methylpropyl (sec-butyl), 2-methylpropyl(isobutyl) or 1,1-dimethylethyl (tert-butyl). C₁-C₆-Alkyl isadditionally also, for example, pentyl, 1-methylbutyl, 2-methylbutyl,3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl,1,2-dimethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl,3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl,1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl,3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl,1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, or1-ethyl-2-methylpropyl. C₁-C₈-Alkyl is additionally also, for example,heptyl, octyl, 2-ethylhexyl and positional isomers thereof. C₁-C₁₀-Alkylis additionally also, for example, nonyl, decyl and positional isomersthereof. C₂-C₄-Alkyl is ethyl, propyl, isopropyl, n-butyl,1-methylpropyl (sec-butyl), 2-methylpropyl (isobutyl) or1,1-dimethylethyl (tert-butyl).

The term “haloalkyl” as used herein, which is also expressed as “alkylwhich is partially or fully halogenated”, refers to straight-chain orbranched alkyl groups having 1 to 2 (“C₁-C₂-haloalkyl”), 1 to 3(“C₁-C₃-haloalkyl”), 1 to 4 (“C₁-C₄-haloalkyl”), 1 to 6(“C₁-C₆-haloalkyl”), 1 to 8 (“C₁-C₈-haloalkyl”) or 1 to 10(“C₁-C₁₀-haloalkyl”) carbon atoms (as mentioned above), where some orall of the hydrogen atoms in these groups are replaced by halogen atomsas mentioned above: in particular C₁-C₂-haloalkyl, such as chloromethyl,bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl,difluoromethyl, trifluoromethyl, chlorofluoromethyl,dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl,1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl.C₁-C₃-haloalkyl is additionally, for example, 1-fluoropropyl,2-fluoropropyl, 3-fluoropropyl, 1,1-difluoropropyl, 2,2-difluoropropyl,1,2-difluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl,heptafluoropropyl, 1,1,1-trifluoroprop-2-yl, 3-chloropropyl and thelike. Examples for C₁-C₄-haloalkyl are, apart those mentioned forC₁-C₃-haloalkyl, 4-chlorobutyl and the like.

“Halomethyl” is methyl in which 1, 2 or 3 of the hydrogen atoms arereplaced by halogen atoms. Examples are bromomethyl, chloromethyl,fluoromethyl, dichloromethyl, trichloromethyl, difluoromethyl,trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl,chlorodifluoromethyl and the like.

The term “alkenyl” as used herein refers to monounsaturatedstraight-chain or branched hydrocarbon radicals having 2 to 3(“C₂-C₃-alkenyl”), 2 to 4 (“C₂-C₄-alkenyl”), 2 to 6 (“C₂-C₆-alkenyl”), 2to 8 (“C₂-C₈-alkenyl”) or 2 to 10 (“C₂-C₁₀-alkenyl”) carbon atoms and adouble bond in any position, for example C₂-C₃-alkenyl, such as ethenyl,1-propenyl, 2-propenyl or 1-methylethenyl; C₂-C₄-alkenyl, such asethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl,3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenylor 2-methyl-2-propenyl; C₂-C₆-alkenyl, such as ethenyl, 1-propenyl,2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl,1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl,2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl,1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl,1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl,1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl,1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl,1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl,1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl,1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl,4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl,3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl,2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl,1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl,4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl,1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl,1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl,2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl,2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl,1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl,2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl,1-ethyl-2-methyl-1-propenyl, 1-ethyl-2-methyl-2-propenyl and the like,or C₂-C₁₀-alkenyl, such as the radicals mentioned for C₂-C₆-alkenyl andadditionally 1-heptenyl, 2-heptenyl, 3-heptenyl, 1-octenyl, 2-octenyl,3-octenyl, 4-octenyl, 1-nonenyl, 2-nonenyl, 3-nonenyl, 4-nonenyl,1-decenyl, 2-decenyl, 3-decenyl, 4-decenyl, 5-decenyl and the positionalisomers thereof.

The term “haloalkenyl” as used herein, which is also expressed as“alkenyl which is partially or fully halogenated”, refers to unsaturatedstraight-chain or branched hydrocarbon radicals having 2 to 3(“C₂-C₃-haloalkenyl”), 2 to 4 (“C₂-C₄-haloalkenyl”), 2 to 6(“C₂-C₆-haloalkenyl”), 2 to 8 (“C₂-C₆-haloalkenyl”) or 2 to 10(“C₂-C₁₀-haloalkenyl”) carbon atoms and a double bond in any position(as mentioned above), where some or all of the hydrogen atoms in thesegroups are replaced by halogen atoms as mentioned above, in particularfluorine, chlorine and bromine, for example chlorovinyl, chloroallyl andthe like.

The term “alkynyl” as used herein refers to straight-chain or branchedhydrocarbon groups having 2 to 3 (“C₂-C₃-alkynyl”), 2 to 4(“C₂-C₄-alkynyl”), 2 to 6 (“C₂-C₆-alkynyl”), 2 to 8 (“C₂-C₈-alkynyl”),or 2 to 10 (“C₂-C₁₀-alkynyl”) carbon atoms and one or two triple bondsin any position, for example C₂-C₃-alkynyl, such as ethynyl, 1-propynylor 2-propynyl; C₂-C₄-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl,1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl and the like,C₂-C₆-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl,2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl,3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl,2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl,1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl,5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl,1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl,3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl,4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl,1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl,1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl,1-ethyl-1-methyl-2-propynyl and the like;

The term “haloalkynyl” as used herein, which is also expressed as“alkynyl which is partially or fully halogenated”, refers to unsaturatedstraight-chain or branched hydrocarbon radicals having 2 to 3(“C₂-C₃-haloalkynyl”), 2 to 4 (“C₂-C₄-haloalkynyl”), 3 to 4(“C₃-C₄-haloalkynyl”), 2 to 6 (“C₂-C₆-haloalkynyl”), 2 to 8(“C₂-C₈-haloalkynyl”) or 2 to 10 (“C₂-C₁₀-haloalkynyl”) carbon atoms andone or two triple bonds in any position (as mentioned above), where someor all of the hydrogen atoms in these groups are replaced by halogenatoms as mentioned above, in particular fluorine, chlorine and bromine;

The term “cycloalkyl” as used herein refers to mono- or bi- orpolycyclic saturated hydrocarbon radicals having 3 to 8(“C₃-C₈-cycloalkyl”), in particular 3 to 6 (“C₃-C₆-cycloalkyl”) or 3 to5 (“C₃-C₅-cycloalkyl”) or 3 to 4 (“C₃-C₄-cycloalkyl”) carbon atoms.Examples of monocyclic radicals having 3 to 4 carbon atoms comprisecyclopropyl and cyclobutyl. Examples of monocyclic radicals having 3 to5 carbon atoms comprise cyclopropyl, cyclobutyl and cyclopentyl.Examples of monocyclic radicals having 3 to 6 carbon atoms comprisecyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Examples ofmonocyclic radicals having 3 to 8 carbon atoms comprise cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.Examples of bicyclic radicals having 7 or 8 carbon atoms comprisebicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl, bicyclo[2.2.2]octyl andbicyclo[3.2.1]octyl. Preferably, the term cycloalkyl denotes amonocyclic saturated hydrocarbon radical.

The term “halocycloalkyl” as used herein, which is also expressed as“cycloalkyl which is partially or fully halogenated”, refers to mono- orbi- or polycyclic saturated hydrocarbon groups having 3 to 8(“C₃-C₈-halocycloalkyl”) or preferably 3 to 6 (“C₃-C₆-halocycloalkyl”)or 3 to 5 (“C₃-C₅-halocycloalkyl”) or 3 to 4 (“C₃-C₄-halocycloalkyl”)carbon ring members (as mentioned above) in which some or all of thehydrogen atoms are replaced by halogen atoms as mentioned above, inparticular fluorine, chlorine and bromine.

The term “cycloalkyl-C₁-C₄-alkyl” refers to a C₃-C₈-cycloalkyl group(“C₃-C₈-cycloalkyl-C₁-C₄-alkyl”), preferably a C₃-C₆-cycloalkyl group(“C₃-C₆-cycloalkyl-C₁-C₄-alkyl”), more preferably a C₃-C₄-cycloalkylgroup (“C₃-C₄-cycloalkyl-C₁-C₄-alkyl”) as defined above (preferably amonocyclic cycloalkyl group) which is bound to the remainder of themolecule via a C₁-C₄-alkyl group, as defined above. Examples forC₃-C₄-cycloalkyl-C₁-C₄-alkyl are cyclopropylmethyl, cyclopropylethyl,cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl andcyclobutylpropyl, Examples for C₃-C₆-cycloalkyl-C₁-C₄-alkyl, apart thosementioned for C₃-C₄-cycloalkyl-C₁-C₄-alkyl, are cyclopentylmethyl,cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyland cyclohexylpropyl. Examples for C₃-C₈-cycloalkyl-C₁-C₄-alkyl, apartthose mentioned for C₃-C₆-cycloalkyl-C₁-C₄-alkyl, are cycloheptylmethyl,cycloheptylethyl, cyclooctylmethyl and the like.

The term “C₃-C₆-cycloalkyl-methyl” refers to a C₃-C₆-cycloalkyl groupwhich is bound to the remainder of the molecule via a methylene group(CH₂). Examples are cyclopropylmethyl, cyclobutylmethyl,cyclopentylmethyl and cyclohexylmethyl.

The term “C₃-C₈-halocycloalkyl-C₁-C₄-alkyl” refers to aC₃-C₈-halocycloalkyl group as defined above which is bound to theremainder of the molecule via a C₁-C₄-alkyl group, as defined above.

The term “C₁-C₂-alkoxy” is a C₁-C₂-alkyl group, as defined above,attached via an oxygen atom. The term “C₁-C₃-alkoxy” is a C₁-C₃-alkylgroup, as defined above, attached via an oxygen atom. The term“C₁-C₄-alkoxy” is a C₁-C₄-alkyl group, as defined above, attached via anoxygen atom. The term “C₁-C₆-alkoxy” is a C₁-C₆-alkyl group, as definedabove, attached via an oxygen atom. The term “C₁-C₁₀-alkoxy” is aC₁-C₀-alkyl group, as defined above, attached via an oxygen atom.C₁-C₂-Alkoxy is methoxy or ethoxy. C₁-C₃-Alkoxy is additionally, forexample, n-propoxy and 1-methylethoxy (isopropoxy). C₁-C₄-Alkoxy isadditionally, for example, butoxy, 1-methylpropoxy (sec-butoxy),2-methylpropoxy (isobutoxy) or 1,1-dimethylethoxy (tert-butoxy).C₁-C₆-Alkoxy is additionally, for example, pentoxy, 1-methylbutoxy,2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy,1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy,1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy,1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy,2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy,1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy,1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or1-ethyl-2-methylpropoxy. C₁-C₈-Alkoxy is additionally, for example,heptyloxy, octyloxy, 2-ethylhexyloxy and positional isomers thereof.C₁-C₁₀-Alkoxy is additionally, for example, nonyloxy, decyloxy andpositional isomers thereof.

The term “C₁-C₂-haloalkoxy” is a C₁-C₂-haloalkyl group, as definedabove, attached via an oxygen atom. The term “C₁-C₃-haloalkoxy” is aC₁-C₃-haloalkyl group, as defined above, attached via an oxygen atom.The term “C₁-C₄-haloalkoxy” is a C₁—C₄-haloalkyl group, as definedabove, attached via an oxygen atom. The term “C₁-C₆-haloalkoxy” is aC₁-C₆-haloalkyl group, as defined above, attached via an oxygen atom.The term “C₁-C₁₀-haloalkoxy” is a C₁-C₁₀-haloalkyl group, as definedabove, attached via an oxygen atom. C₁-C₂-Haloalkoxy is, for example,OCH₂F, OCHF₂, OCF₃, OCH₂Cl, OCHCl₂, OCCl₃, chlorofluoromethoxy,dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy,2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy,2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,2,2,2-trichloroethoxy or OC₂F₅. C₁-C₃-Haloalkoxy is additionally, forexample, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy,2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy,2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy,3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH₂—C₂F₅, OCF₂—C₂F₅,1-(CH₂F)-2-fluoroethoxy, 1-(CH₂Cl)-2-chloroethoxy or1-(CH₂Br)-2-bromoethoxy. C₁-C₄-Haloalkoxy is additionally, for example,4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy.C₁-C₆-Haloalkoxy is additionally, for example, 5-fluoropentoxy,5-chloropentoxy, 5-brompentoxy, 5-iodopentoxy, undecafluoropentoxy,6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy ordodecafluorohexoxy.

The term “C₁-C₃-alkoxy-C₁-C₃-alkyl” as used herein, refers to astraight-chain or branched alkyl group having 1 to 3 carbon atoms, asdefined above, where one hydrogen atom is replaced by a C₁-C₃-alkoxygroup, as defined above. The term “C₁-C₄-alkoxy-C₁-C₄-alkyl” as usedherein, refers to a straight-chain or branched alkyl group having 1 to 4carbon atoms, as defined above, where one hydrogen atom is replaced by aC₁-C₄-alkoxy group, as defined above. The term“C₁-C₆-alkoxy-C₁-C₆-alkyl” as used herein, refers to a straight-chain orbranched alkyl group having 1 to 6 carbon atoms, as defined above, whereone hydrogen atom is replaced by a C₁-C₆-alkoxy group, as defined above.Examples are methoxymethyl, ethoxymethyl, propoxymethyl,isopropoxymethyl, n-butoxymethyl, sec-butoxymethyl, isobutoxymethyl,tert-butoxymethyl, 1-methoxyethyl, 1-ethoxyethyl, 1-propoxyethyl,1-isopropoxyethyl, 1-n-butoxyethyl, 1-sec-butoxyethyl, 1-isobutoxyethyl,1-tert-butoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl,2-isopropoxyethyl, 2-n-butoxyethyl, 2-sec-butoxyethyl, 2-isobutoxyethyl,2-tert-butoxyethyl, 1-methoxypropyl, 1-ethoxypropyl, 1-propoxypropyl,1-isopropoxypropyl, 1-n-butoxypropyl, 1-sec-butoxypropyl,1-isobutoxypropyl, 1-tert-butoxypropyl, 2-methoxypropyl, 2-ethoxypropyl,2-propoxypropyl, 2-isopropoxypropyl, 2-n-butoxypropyl,2-sec-butoxypropyl, 2-isobutoxypropyl, 2-tert-butoxypropyl,3-methoxypropyl, 3-ethoxypropyl, 3-propoxypropyl, 3-isopropoxypropyl,3-n-butoxypropyl, 3-sec-butoxypropyl, 3-isobutoxypropyl,3-tert-butoxypropyl and the like.

The term “C₁-C₄-alkoxy-methyl” as used herein, refers to methyl in whichone hydrogen atom is replaced by a C₁-C₄-alkoxy group, as defined above.The term “C₁-C₆-alkoxy-methyl” as used herein, refers to methyl in whichone hydrogen atom is replaced by a C₁-C₆-alkoxy group, as defined above.Examples are methoxymethyl, ethoxymethyl, propoxymethyl,isopropoxymethyl, n-butoxymethyl, sec-butoxymethyl, isobutoxymethyl,tert-butoxymethyl, pentyloxymethyl, hexyloxymethyl and the like.

C₁-C₆-Haloalkoxy-C₁-C₆-alkyl is a straight-chain or branched alkyl grouphaving from 1 to 6, especially 1 to 4 carbon atoms(═C₁-C₆-haloalkoxy-C₁-C₄-alkyl), wherein one of the hydrogen atoms isreplaced by a C₁-C₆-alkoxy group and wherein at least one, e.g. 1, 2, 3,4 or all of the remaining hydrogen atoms (either in the alkoxy moiety orin the alkyl moiety or in both) are replaced by halogen atoms.C₁-C₄-Haloalkoxy-C₁-C₄-alkyl is a straight-chain or branched alkyl grouphaving from 1 to 4 carbon atoms, wherein one of the hydrogen atoms isreplaced by a C₁-C₄-alkoxy group and wherein at least one, e.g. 1, 2, 3,4 or all of the remaining hydrogen atoms (either in the alkoxy moiety orin the alkyl moiety or in both) are replaced by halogen atoms. Examplesare difluoromethoxymethyl (CH F₂OCH₂), trifluoromethoxymethyl,1-difluoromethoxyethyl, 1-trifluoromethoxyethyl, 2-difluoromethoxyethyl,2-trifluoromethoxyethyl, difluoro-methoxymethyl (CH₃OCF₂),1,1-difluoro-2-methoxyethyl, 2,2-difluoro-2-methoxyethyl and the like.

The term “C₁-C₂-alkylthio” is a C₁-C₂-alkyl group, as defined above,attached via a sulfur atom. The term “C₁-C₃-alkylthio” is a C₁-C₃-alkylgroup, as defined above, attached via a sulfur atom. The term“C₁-C₄-alkylthio” is a C₁-C₄-alkyl group, as defined above, attached viaa sulfur atom. The term “C₁-C₆-alkylthio” is a C₁-C₆-alkyl group, asdefined above, attached via a sulfur atom. The term “C₁-C₁₀-alkylthio”is a C₁-C₁₀-alkyl group, as defined above, attached via a sulfur atom.C₁-C₂-Alkylthio is methylthio or ethylthio. C₁-C₃-Alkylthio isadditionally, for example, n-propylthio or 1-methylethylthio(isopropylthio). C₁-C₄-Alkylthio is additionally, for example,butylthio, 1-methylpropylthio (sec-butylthio), 2-methylpropylthio(isobutylthio) or 1,1-dimethylethylthio (tert-butylthio).C₁-C₆-Alkylthio is additionally, for example, pentylthio,1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio,1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 2,2-dimethylpropylthio,1-ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio,3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio,1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio,2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio,2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio,1-ethyl-1-methylpropylthio or 1-ethyl-2-methylpropylthio.C₁-C₈-Alkylthio is additionally, for example, heptylthio, octylthio,2-ethylhexylthio and positional isomers thereof. C₁-C₁₀-Alkylthio isadditionally, for example, nonylthio, decylthio and positional isomersthereof.

The term “C₁-C₂-haloalkylthio” is a C₁-C₂-haloalkyl group, as definedabove, attached via a sulfur atom. The term “C₁-C₃-haloalkylthio” is aC₁-C₃-haloalkyl group, as defined above, attached via a sulfur atom. Theterm “C₁-C₄-haloalkylthio” is a C₁-C₄-haloalkyl group, as defined above,attached via a sulfur atom. The term “C₁-C₆-haloalkylthio” is aC₁-C₆-haloalkyl group, as defined above, attached via a sulfur atom. Theterm “C₁-C₁₀-haloalkylthio” is a C₁-C₁₀-haloalkyl group, as definedabove, attached via a sulfur atom. C₁-C₂-Haloalkylthio is, for example,SCH₂F, SCHF₂, SCF₃, SCH₂C₁, SCHCl₂, SCCl₃, chlorofluoromethylthio,dichlorofluoromethylthio, chlorodifluoromethylthio, 2-fluoroethylthio,2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio,2,2-difluoroethylthio, 2,2,2-trifluoroethylthio,2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio,2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio or SC₂F₅.C₁-C₃-Haloalkylthio is additionally, for example, 2-fluoropropylthio,3-fluoropropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio,2-chloropropylthio, 3-chloropropylthio, 2,3-dichloropropylthio,2-bromopropylthio, 3-bromopropylthio, 3,3,3-trifluoropropylthio,3,3,3-trichloropropylthio, SCH₂—C₂F₅, SCF₂—C₂F₅,1-(CH₂F)-2-fluoroethylthio, 1-(CH₂C₁)-2-chloroethylthio or1-(CH₂Br)-2-bromoethylthio. C₁-C₄-Haloalkylthio is additionally, forexample, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio ornonafluorobutylthio. C₁-C₆-Haloalkylthio is additionally, for example,5-fluoropentylthio, 5-chloropentylthio, 5-brompentylthio,5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio,6-chlorohexylthio, 6-bromohexylthio, 6-iodohexylthio ordodecafluorohexylthio.

The term “C₁-C₂-alkylsulfinyl” is a C₁-C₂-alkyl group, as defined above,attached via a sulfinyl [S(O)] group. The term “C₁-C₄-alkylsulfinyl” isa C₁-C₄-alkyl group, as defined above, attached via a sulfinyl [S(O)]group. The term “C₁-C₆-alkylsulfinyl” is a C₁-C₆-alkyl group, as definedabove, attached via a sulfinyl [S(O)] group. The term“C₁-C₁₀-alkylsulfinyl” is a C₁-C₀-alkyl group, as defined above,attached via a sulfinyl [S(O)] group. C₁-C₂-Alkylsulfinyl ismethylsulfinyl or ethylsulfinyl. C₁-C₄-Alkylsulfinyl is additionally,for example, n-propylsulfinyl, 1-methylethylsulfinyl(isopropylsulfinyl), butylsulfinyl, 1-methylpropylsulfinyl(sec-butylsulfinyl), 2-methylpropylsulfinyl (isobutylsulfinyl) or1,1-dimethylethylsulfinyl (tert-butylsulfinyl). C₁-C₆-Alkylsulfinyl isadditionally, for example, pentylsulfinyl, 1-methylbutylsulfinyl,2-methylbutylsulfinyl, 3-methyl butylsulfinyl,1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl,2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, hexylsulfinyl,1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl,4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl,1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl,2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl,3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethyl butylsulfinyl,1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl,1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl.C₁-C₈-Alkylsulfinyl is additionally, for example, heptylsulfinyl,octylsulfinyl, 2-ethylhexylsulfinyl and positional isomers thereof.C₁-C₁₀-Alkylsulfinyl is additionally, for example, nonylsulfinyl,decylsulfinyl and positional isomers thereof.

The term “C₁-C₂-haloalkylsulfinyl” is a C₁-C₂-haloalkyl group, asdefined above, attached via a sulfinyl [S(O)] group. The term“C₁-C₄-haloalkylsulfinyl” is a C₁-C₄-haloalkyl group, as defined above,attached via a sulfinyl [S(O)] group. The term “C₁—C₆-haloalkylsulfinyl”is a C₁-C₆-haloalkyl group, as defined above, attached via a sulfinyl[S(O)] group. The term “C₁-C₁₀-haloalkylsulfinyl” is a C₁-C₁₀-haloalkylgroup, as defined above, attached via a sulfinyl [S(O)] group.C₁-C₂-Haloalkylsulfinyl is, for example, S(O)CH₂F, S(O)CH F₂, S(O)CF₃,S(O)CH₂C₁, S(O)CHCl₂, S(O)CCl₃, chlorofluoromethylsulfinyl,dichlorofluoromethylsulfinyl, chlorodifluoromethylsulfinyl,2-fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl,2-iodoethylsulfinyl, 2,2-difluoroethylsulfinyl,2,2,2-trifluoroethylsulfinyl, 2-chloro-2-fluoroethylsulfinyl,2-chloro-2,2-difluoroethylsulfinyl, 2,2-dichloro-2-fluoroethylsulfinyl,2,2,2-trichloroethylsulfinyl or S(O)C₂F₅. C₁-C₄-Haloalkylsulfinyl isadditionally, for example, 2-fluoropropylsulfinyl,3-fluoropropylsulfinyl, 2,2-difluoropropylsulfinyl,2,3-difluoropropylsulfinyl, 2-chloropropylsulfinyl,3-chloropropylsulfinyl, 2,3-dichloropropylsulfinyl,2-bromopropylsulfinyl, 3-bromopropylsulfinyl,3,3,3-trifluoropropylsulfinyl, 3,3,3-trichloropropylsulfinyl,S(O)CH₂—C₂F₅, S(O)CF₂—C₂F₅, 1-(CH₂F)-2-fluoroethylsulfinyl,1-(CH₂Cl)-2-chloroethylsulfinyl, 1-(CH₂Br)-2-bromoethylsulfinyl,4-fluorobutylsulfinyl, 4-chlorobutylsulfinyl, 4-bromobutylsulfinyl ornonafluorobutylsulfinyl. C₁-C₆-Haloalkylsulfinyl is additionally, forexample, 5-fluoropentylsulfinyl, 5-chloropentylsulfinyl,5-brompentylsulfinyl, 5-iodopentylsulfinyl, undecafluoropentylsulfinyl,6-fluorohexylsulfinyl, 6-chlorohexylsulfinyl, 6-bromohexylsulfinyl,6-iodohexylsulfinyl or dodecafluorohexylsulfinyl.

The term “C₁-C₂-alkylsulfonyl” is a C₁-C₂-alkyl group, as defined above,attached via a sulfonyl [S(O)₂] group. The term “C₁-C₃-alkylsulfonyl” isa C₁-C₃-alkyl group, as defined above, attached via a sulfonyl [S(O)₂]group. The term “C₁-C₄-alkylsulfonyl” is a C₁-C₄-alkyl group, as definedabove, attached via a sulfonyl [S(O)₂] group. The term“C₁-C₆-alkylsulfonyl” is a C₁-C₆-alkyl group, as defined above, attachedvia a sulfonyl [S(O)₂] group. The term “C₁-C₁₀-alkylsulfonyl” is aC₁-C₁₀-alkyl group, as defined above, attached via a sulfonyl [S(O)₂]group. C₁-C₂-Alkylsulfonyl is methylsulfonyl or ethylsulfonyl.C₁-C₃-Alkylsulfonyl is additionally, for example, n-propylsulfonyl or1-methylethylsulfonyl (isopropylsulfonyl). C₁-C₄-Alkylsulfonyl isadditionally, for example, butylsulfonyl, 1-methylpropylsulfonyl(sec-butylsulfonyl), 2-methylpropylsulfonyl (isobutylsulfonyl) or1,1-dimethylethylsulfonyl (tert-butylsulfonyl). C₁-C₆-Alkylsulfonyl isadditionally, for example, pentylsulfonyl, 1-methylbutylsulfonyl,2-methylbutylsulfonyl, 3-methylbutylsulfonyl,1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl,2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl,1-methyl pentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl,4-methyl pentylsulfonyl, 1,1-dimethylbutylsulfonyl,1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl,2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl,3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl,1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl,1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl.C₁-C₈-Alkylsulfonyl is additionally, for example, heptylsulfonyl,octylsulfonyl, 2-ethylhexylsulfonyl and positional isomers thereof.C₁-C₁₀-Alkylsulfonyl is additionally, for example, nonylsulfonyl,decylsulfonyl and positional isomers thereof.

The term “C₁-C₂-haloalkylsulfonyl” is a C₁-C₂-haloalkyl group, asdefined above, attached via a sulfonyl [S(O)₂] group. The term“C₁-C₃-haloalkylsulfonyl” is a C₁-C₃-haloalkyl group, as defined above,attached via a sulfonyl [S(O)₂] group. The term“C₁-C₄-haloalkylsulfonyl” is a C₁-C₄-haloalkyl group, as defined above,attached via a sulfonyl [S(O)₂] group. The term“C₁-C₆-haloalkylsulfonyl” is a C₁-C₆-haloalkyl group, as defined above,attached via a sulfonyl [S(O)₂] group. The term“C₁-C₁₀-haloalkylsulfonyl” is a C₁-C₁₀-haloalkyl group, as definedabove, attached via a sulfonyl [S(O)₂] group. C₁-C₂-Haloalkylsulfonylis, for example, S(O)₂CH₂F, S(O)₂CHF₂, S(O)₂CF₃, S(O)₂CH₂C₁, S(O)₂CHCl₂,S(O)₂CCl₃, chlorofluoromethylsulfonyl, dichlorofluoromethylsulfonyl,chlorodifluoromethylsulfonyl, 2-fluoroethylsulfonyl,2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl,2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl,2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl,2,2-dichloro-2-fluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl orS(O)₂C₂F₅. C₁-C₃-Haloalkylsulfonyl is additionally, for example,2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl,2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl,2-chloropropylsulfonyl, 3-chloropropylsulfonyl,2,3-dichloropropylsulfonyl, 2-bromopropylsulfonyl,3-bromopropylsulfonyl, 3,3,3-trifluoropropylsulfonyl,3,3,3-trichloropropylsulfonyl, S(O)₂CH₂—C₂F₅, S(O)₂CF₂—C₂F₅,1-(CH₂F)-2-fluoroethylsulfonyl, 1-(CH₂C₁)-2-chloroethylsulfonylor1-(CH₂Br)-2-bromoethylsulfonyl. C₁-C₄-Haloalkylsulfonyl is additionally,for example, 4-fluorobutylsulfonyl, 4-chlorobutylsulfonyl,4-bromobutylsulfonyl or nonafluorobutylsulfonyl. C₁-C₆-Haloalkylsulfonylis additionally, for example, 5-fluoropentylsulfonyl,5-chloropentylsulfonyl, 5-brompentylsulfonyl, 5-iodopentylsulfonyl,undecafluoropentylsulfonyl, 6-fluorohexylsulfonyl,6-chlorohexylsulfonyl, 6-bromohexylsulfonyl, 6-iodohexylsulfonyl ordodecafluorohexylsulfonyl.

The substituent “oxo” replaces a CH₂ group by a C(═O) group.

The term “alkylcarbonyl” is a C₁-C₆-alkyl (“C₁-C₆-alkylcarbonyl”),preferably a C₁-C₄-alkyl (“C₁-C₄-alkylcarbonyl”) group, as definedabove, attached via a carbonyl [C(═O)] group. Examples are acetyl(methylcarbonyl), propionyl (ethylcarbonyl), propylcarbonyl,isopropylcarbonyl, n-butylcarbonyl and the like.

The term “haloalkylcarbonyl” is a C₁-C₆-haloalkyl(“C₁-C₆-haloalkylcarbonyl”), preferably a C₁-C₄-haloalkyl(“C₁-C₄-haloalkylcarbonyl”) group, as defined above, attached via acarbonyl [C(═O)] group. Examples are trifluoromethylcarbonyl,2,2,2-trifluoroethylcarbonyl and the like.

The term “alkoxycarbonyl” is a C₁-C₆-alkoxy (“C₁-C₆-alkoxycarbonyl”),preferably a C₁-C₄-alkoxy (“C₁-C₄-alkoxycarbonyl”) group, as definedabove, attached via a carbonyl [C(═O)] group. Examples aremethoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl,n-butoxycarbonyl and the like.

The term “haloalkoxycarbonyl” is a C₁-C₆-haloalkoxy(“C₁-C₆-haloalkoxycarbonyl”), preferably a C₁-C₄-haloalkoxy(“C₁-C₄-haloalkoxycarbonyl”) group, as defined above, attached via acarbonyl [C(═O)] group. Examples are trifluoromethoxycarbonyl,2,2,2-trifluoroethoxycarbonyl and the like.

The term “C₁-C₆-alkylamino” is a group —N(H)C₁-C₆-alkyl. Examples aremethylamino, ethylamino, propylamino, isopropylamino, butylamino and thelike.

The term “di-(C₁-C₆-alkyl)amino” is a group —N(C₁-C₆-alkyl)₂. Examplesare dimethylamino, diethylamino, ethylmethylamino, dipropylamino,diisopropylamino, methylpropylamino, methylisopropylamino,ethylpropylamino, ethylisopropylamino, dibutylamino and the like.

The term “aminocarbonyl” is a group —C(═O)—NH₂.

The term “C₁-C₄-alkylaminocarbonyl” is a group —C(═O)—N(H)C₁-C₄-alkyl.The term “C₁-C₆-alkylaminocarbonyl” is a group —C(═O)—N(H)C₁-C₆-alkyl.Examples are methylaminocarbonyl, ethylaminocarbonyl,propylaminocarbonyl, isopropylaminocarbonyl, butylaminocarbonyl and thelike.

The term “di-(C₁-C₄-alkyl)aminocarbonyl” is a group—C(═O)—N(C₁-C₄-alkyl)₂. The term “di-(C₁-C₆-alkyl)aminocarbonyl” is agroup —C(═O)—N(C₁-C₆-alkyl)₂. Examples are dimethylaminocarbonyl,diethylaminocarbonyl, ethylmethylaminocarbonyl, dipropylaminocarbonyl,diisopropylaminocarbonyl, methylpropylaminocarbonyl,methylisopropylaminocarbonyl, ethyl propylaminocarbonyl,ethylisopropylaminocarbonyl, dibutylaminocarbonyl and the like.

The term “3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated, partiallyunsaturated or maximally unsaturated heterocyclic ring containing 1, 2or 3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO,SO and SO₂, as ring members” denotes a 3-, 4-, 5-, 6- or 7-memberedsaturated, partially unsaturated or maximum unsaturated heteromonocyclicring or a 8-, 9- or 10-membered saturated, partially unsaturated ormaximally unsaturated heterobicyclic ring containing 1, 2 or 3 (or 4)heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO₂,as ring members.

Unsaturated rings contain at least one C—C and/or C—N and/or N—N doublebond(s). Maximally unsaturated rings contain as many conjugated C—Cand/or C—N and/or N—N double bonds as allowed by the ring size.Maximally unsaturated 5- or 6-membered heterocyclic rings are aromatic.The heterocyclic ring may be attached to the remainder of the moleculevia a carbon ring member or via a nitrogen ring member. As a matter ofcourse, the heterocyclic ring contains at least one carbon ring atom. Ifthe ring contains more than one O ring atom, these are not adjacent.

The term “3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturatedor maximum unsaturated heterocyclic ring containing 1, 2 or 3 (or 4)heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO₂,as ring members” [wherein “maximum unsaturated” includes also“aromatic”] as used herein denotes monocyclic radicals, the monocyclicradicals being saturated, partially unsaturated or maximum unsaturated(including aromatic). The term “3-, 4-, 5-, 6-, 7- or 8-memberedsaturated, partially unsaturated or maximum unsaturated heterocyclicring containing 1, 2 or 3 (or 4) heteroatoms or heteroatom groupsselected from N, O, S, NO, SO and SO₂, as ring members” [wherein“maximum unsaturated” includes also “aromatic”] as used herein furtheralso encompasses 8-membered heteromonocyclic radicals containing 1, 2 or3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO, SOand SO₂, as ring members, the monocyclic radicals being saturated,partially unsaturated or maximum unsaturated (including aromatic).Unsaturated rings contain at least one C—C and/or C—N and/or N—N doublebond(s). Maximum unsaturated rings contain as many conjugated C—C and/orC—N and/or N—N double bonds as allowed by the ring size. Maximumunsaturated 5- or 6-membered heterocyclic rings are aromatic. 7- and8-membered rings cannot be aromatic. They are homoaromatic (7-memberedring, 3 double bonds) or have 4 double bonds (8-membered ring). Theheterocyclic ring may be attached to the remainder of the molecule via acarbon ring member or via a nitrogen ring member. As a matter of course,the heterocyclic ring contains at least one carbon ring atom. If thering contains more than one O ring atom, these are not adjacent.

Examples of a 3-, 4-, 5-, 6- or 7-membered saturated heterocyclic ringinclude: Oxiranyl, thiiranyl, aziridinyl, oxetanyl, thietanyl,azetidinyl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl,tetrahydrothien-2-yl, tetrahydrothien-3-yl, pyrrolidin-1-yl,pyrrolidin-2-yl, pyrrolidin-3-yl, pyrazolidin-1-yl, pyrazolidin-3-yl,pyrazolidin-4-yl, pyrazolidin-5-yl, imidazolidin-1-yl,imidazolidin-2-yl, imidazolidin-4-yl, oxazolidin-2-yl, oxazolidin-3-yl,oxazolidin-4-yl, oxazolidin-5-yl, isoxazolidin-2-yl, isoxazolidin-3-yl,isoxazolidin-4-yl, isoxazolidin-5-yl, thiazolidin-2-yl,thiazolidin-3-yl, thiazolidin-4-yl, thiazolidin-5-yl,isothiazolidin-2-yl, isothiazolidin-3-yl, isothiazolidin-4-yl,isothiazolidin-5-yl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl,1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl,1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl,1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-1-yl,1,3,4-triazolidin-2-yl, 1,2,3,4-tetrazolidin-1-yl,1,2,3,4-tetrazolidin-2-yl, 1,2,3,4-tetrazolidin-5-yl,2-tetrahydropyranyl, 4-tetrahydropyranyl, 1,3-dioxan-5-yl,1,4-dioxan-2-yl, piperidin-1-yl, piperidin-2-yl, piperidin-3-yl,piperidin-4-yl, hexahydropyridazin-3-yl, hexahydropyridazin-4-yl,hexahydropyrimidin-2-yl, hexahydropyrimidin-4-yl,hexahydropyrimidin-5-yl, piperazin-1-yl, piperazin-2-yl,1,3,5-hexahydrotriazin-1-yl, 1,3,5-hexahydrotriazin-2-yl and1,2,4-hexahydrotriazin-3-yl, morpholin-2-yl, morpholin-3-yl,morpholin-4-yl, thiomorpholin-2-yl, thiomorpholin-3-yl,thiomorpholin-4-yl, 1-oxothiomorpholin-2-yl, 1-oxothiomorpholin-3-yl,1-oxothiomorpholin-4-yl, 1,1-dioxothiomorpholin-2-yl,1,1-dioxothiomorpholin-3-yl, 1,1-dioxothiomorpholin-4-yl, azepan-1-,-2-, -3- or -4-yl, oxepan-2-, -3-, -4- or -5-yl,hexahydro-1,3-diazepinyl, hexahydro-1,4-diazepinyl,hexahydro-1,3-oxazepinyl, hexahydro-1,4-oxazepinyl,hexahydro-1,3-dioxepinyl, hexahydro-1,4-dioxepinyl and the like.

Examples of a 3-, 4-, 5-, 6- or 7-membered partially unsaturatedheterocyclic ring include: 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl,2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl,2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl,2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl,2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl,2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl,2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl,2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl,2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl,2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl,2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl,2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl,2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl,3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl,3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl,4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl,4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl,2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl,3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl,3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl,2,3-dihydro-1,2,4-triazol-1-, -2-, -3- or -5-yl,4,5-dihydro-1,3,4-triazol-1-, -2-, -4- or -5-yl,2,5-dihydro-1,3,4-triazol-1-, -2- or -5-yl,4,5-dihydro-1,2,3-triazol-1-, -4- or -5-yl,2,5-dihydro-1,2,3-triazol-1-, -2- or -5-yl,2,3-dihydro-1,2,3-triazol-1-, -2-, -3-, -4- or -5-yl,2,3-dihydro-1,2,3,4-tetrazol-1-, -2-, -3- or -5-yl,2,5-dihydro-1,2,3,4-tetrazol-1-, -2- or -5-yl,4,5-dihydro-1,2,3,4-tetrazol-1-, -4- or -5-yl, 2-, 3-, 4-, 5- or 6-di-or tetrahydropyridinyl, 3-di- or tetrahydropyridazinyl, 4-di- ortetrahydropyridazinyl, 2-di- or tetrahydropyrimidinyl, 4-di- ortetrahydropyrimidinyl, 5-di- or tetrahydropyrimidinyl, di- ortetrahydropyrazinyl, 1,3,5-di- or tetrahydrotriazin-2-yl, 1,2,4-di- ortetrahydrotriazin-3-yl, 2,3,4,5-tetrahydro[1H]azepin-1-, -2-, -3-, -4-,-5-, -6- or -7-yl, 3,4,5,6-tetrahydro[2H]azepin-2-, -3-, -4-, -5-, -6-or -7-yl, 2,3,4,7-tetrahydro[1H]azepin-1-, -2-, -3-, -4-, -5-, -6- or-7-yl, 2,3,6,7-tetrahydro[1H]azepin-1-, -2-, -3-, -4-, -5-, -6- or-7-yl, tetrahydrooxepinyl, such as 2,3,4,5-tetrahydro[1H]oxepin-2-, -3-,-4-, -5-, -6- or -7-yl, 2,3,4,7-tetrahydro[1H]oxepin-2-, -3-, -4-, -5-,-6- or -7-yl, 2,3,6,7-tetrahydro[1H]oxepin-2-, -3-, -4-, -5-, -6- or-7-yl, tetrahydro-1,3-diazepinyl, tetrahydro-1,4-diazepinyl,tetrahydro-1,3-oxazepinyl, tetrahydro-1,4-oxazepinyl,tetrahydro-1,3-dioxepinyl and tetrahydro-1,4-dioxepinyl.

Examples for a 3-, 4-, 5-, 6- or 7-membered maximally unsaturated(including aromatic) heterocyclic ring are 5- or 6-memberedheteroaromatic rings, such as 2-furyl, 3-furyl, 2-thienyl, 3-thienyl,1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 1-pyrazolyl, 3-pyrazolyl,4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl,2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 1-imidazolyl, 2-imidazolyl,4-imidazolyl, 1,3,4-triazol-1-yl, 1,3,4-triazol-2-yl,1,2,3,4-1H-tetrazol-1-yl, 1,2,3,4-1H-tetrazol-5-yl,1,2,3,4-2H-tetrazol-2-yl, 1,2,3,4-2H-tetrazol-5-yl, 2-pyridinyl,3-pyridinyl, 4-pyridinyl, 1-oxopyridin-2-yl, 1-oxopyridin-3-yl,1-oxopyridin-4-yl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl,4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl, and also homoaromaticradicals, such as 1H-azepine, 1H-[1,3]-diazepine and 1H-[1,4]-diazepine.

Examples for a 8-, 9- or 10-membered saturated heterobicyclic ringcontaining 1, 2 or 3 (or 4) heteroatoms or heteroatom groups selectedfrom N, O, S, NO, SO and SO₂, as ring members are:

Examples for a 8-, 9- or 10-membered partially unsaturatedheterobicyclic ring containing 1, 2 or 3 (or 4) heteroatoms orheteroatom groups selected from N, O, S, NO, SO and SO₂, as ring membersare:

Examples for a 8-, 9- or 10-membered maximally unsaturatedheterobicyclic ring containing 1, 2 or 3 (or 4) heteroatoms orheteroatom groups selected from N, O, S, NO, SO and SO₂, as ring membersare:

In the above structures # denotes the attachment point to the remainderof the molecule. The attachment point is not restricted to the ring onwhich is shown, but can be on either of the fused rings, and may be on acarbon or on a nitrogen ring atom. If the rings carry one or moresubstituents, these may be bound to carbon and/or to nitrogen ring atoms(if the latter are not part of a double bond).

A saturated 3-, 4-, 5-, 6-, 7-, 8- or 9-membered ring, wherein the ringmay contain 1 or 2 heteroatoms or heteroatom groups selected from O, S,N, NR¹⁴, NO, SO and SO₂ and/or 1 or 2 groups selected from C═O, C═S andC═NR¹⁴ as ring members is either carbocyclic or heterocyclic. Examplesare, in addition to the saturated heteromonocyclic rings mentionedabove, carbocyclic rings, such as cyclopropyl, cyclopropanonyl,cyclobutyl, cyclobutanonyl, cyclopentyl, cyclopentanonyl, cyclohexyl,cyclohexanonyl, cyclohexadienonyl, cycloheptyl, cycloheptanonyl,cyclooctyl, cyclooctanonyl, furan-2-onyl, pyrrolidine-2-onyl,pyrrolidine-2,5-dionyl, piperidine-2-onyl, piperidine-2,6-dionyl and thelike.

The remarks made below concerning preferred embodiments of the variablesof the compounds of formula I, especially with respect to theirsubstituents A, X¹, B¹, B², B³, G¹, G², R^(g1), R^(g2), R¹, R², R^(3a),R^(3b), R^(3c), R^(3d), R⁴, R⁵, R⁶, R⁸, R⁹, R^(9a), R^(9b), R^(101a),R^(101b), R^(102a), R^(102b), R¹¹, R¹³, R^(14a), R^(14b), R¹⁶, m and n,the features of the use and method according to the invention and of thecomposition of the invention are valid both on their own and, inparticular, in every possible combination with each other.

In the heterocyclic rings, R¹¹ and R¹⁶ may be bound to a carbon ringatom or to a secondary nitrogen ring atom (in the latter case thusreplacing for example the hydrogen atom shown in the E-x or F-x rings).If R¹¹ or R¹⁶ are bound to a nitrogen ring atom, R¹¹ and R¹⁶ arepreferably not halogen, cyano, nitro or a radical bound via O or S, suchas —OH, —SH, alkoxy, haloalkoxy, alkylthio, haloalkylthio,alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl or haloalkylsulfonyl.

In one embodiment of the invention X¹ is O.

In another embodiment of the invention X¹ is CH₂.

W is preferably 0.

In one embodiment of the invention (embodiment 1) Y is —OR⁹, wherein R⁹has one of the above general, or, in particular, one of the belowpreferred meanings.

In a preferred embodiment of embodiment 1 (embodiment 1a), R⁹ isselected from hydrogen, C₁-C₆-alkyl and C₁-C₆-haloalkyl.

Compounds I wherein Y is —OR⁹ have biological activity, but areespecially useful as intermediate compounds in the preparation ofcompounds I wherein Y is —N(R⁵)R⁶. Thus, the invention also relates tointermediate compounds I wherein Y is —OR⁹, wherein R⁹ has one of theabove-defined general meanings or, preferably, one of the above-definedpreferred meanings; and to the use of such compounds in the preparationof compounds I wherein Y is —N(R⁵)R⁶.

Compounds I wherein Y is H have biological activity, too, but areespecially useful as intermediate compounds in the preparation ofcompounds I wherein Y is —N(R⁵)R⁶. Thus, the invention also relates tointermediate compounds I wherein Y is hydrogen; and to the use of suchcompounds in the preparation of compounds I wherein Y is —N(R⁵)R⁶.

In another embodiment of the invention (embodiment 2) Y is —N(R⁵)R⁶;wherein R⁵ and R⁶ have one of the above general, or, in particular, oneof the below preferred meanings.

In a preferred embodiment of embodiment 2 (embodiment 2a)

-   R⁵ is hydrogen or C₁-C₃-alkyl;-   R⁶ is selected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,    C₁-C₄-alkyl which carries one radical R⁸, wherein R⁸ is as defined    below; C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,    C₃-C₆-cycloalkyl which may be substituted by 1 or 2 substituents    selected from F, CN and pyridyl;    -   —N(R^(101a))R^(101b), wherein R^(101a) and R^(101b) are as        defined below;    -   —CH═NOR^(9a), wherein R^(9a) is selected from hydrogen,        C₁-C₆-alkyl and C₁-C₆-haloalkyl;    -   phenyl which may be substituted with 1, 2, 3, 4, or 5        substituents R¹¹, wherein R¹¹ is as defined below; and a        heteromonocyclic ring selected from rings of formulae F-1 to        F-57

-   -   where in F-1 to F-57    -   the zigzag line denotes the attachment point to the remainder of        the molecule;    -   k is 0, 1, 2 or 3,    -   n is 0, 1 or 2, and    -   R¹¹ is as defined below;    -   R⁸ is selected from OH, CN, C₃-C₈-cycloalkyl which optionally        carries a CN or CF₃ substituent, C₃-C₈-halocycloalkyl,        C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,        C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,        C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,        C₁-C₆-haloalkylsulfonyl, —C(═O)N(R^(102a))R^(102b), phenyl,        optionally substituted with 1, 2, 3, 4 or 5 substituents R¹⁶,        and a heterocyclic ring selected from rings of formulae E-1 to        E-57 as defined above;        -   wherein        -   R^(102a) in —C(═O)N(R^(102a))R^(102b) as a meaning for R⁸ is            selected from the group consisting of hydrogen and            C₁-C₆-alkyl; and        -   R^(102b) in —C(═O)N(R^(102a))R^(102b) as a meaning for R⁸ is            selected from the group consisting of hydrogen, C₁-C₆-alkyl,            C₁-C₆-haloalkyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl,            C₃-C₆-halocycloalkyl, CH₂—CN, C₁-C₆-alkoxy and            C₁-C₆-haloalkoxy;    -   R^(101a) in —N(R^(101a))R^(101b) as a meaning for R⁶ is selected        from hydrogen and C₁-C₆-alkyl; and    -   R^(101b) in —N(R^(101a))R^(101b) as a meaning for R⁶ is selected        from hydrogen, —C(═O)N(R^(14a))R^(14b), phenyl, optionally        substituted with 1, 2, 3, 4 or 5 substituents R¹⁶, wherein R¹⁶        is as defined below; and a heteroaromatic ring selected from        rings of formulae E-1 to E-42 as defined above;    -   each R¹¹ is independently selected from the group consisting of        halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl,        C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,        C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfinyl,        C₁-C₄-haloalkylsulfinyl, C₁-C₄-alkylsulfonyl,        C₁-C₄-haloalkylsulfonyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,        C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl,        C₂-C₄-haloalkynyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl,        aminocarbonyl, C₁-C₄-alkylaminocarbonyl and        di-(C₁-C₄-alkyl)-aminocarbonyl; or        -   two R¹¹ present on the same carbon atom of a saturated            heterocyclic ring may form together ═O or ═S; or        -   two R¹¹ present on the same S or SO ring member of a            heterocyclic ring may together form a group ═N(C₁-C₆-alkyl),            ═NO(C₁-C₆-alkyl), ═NN(H)(C₁-C₆-alkyl) or ═NN(C₁-C₆-alkyl)₂;    -   R^(14a) in —C(═O)N(R^(14a))R^(14b) as a meaning for R^(102b) is        selected from the group consisting of hydrogen and C₁-C₆-alkyl;        and    -   R^(14b) in —C(═O)N(R^(14a))R^(14b) as a meaning for R^(102b) is        selected from the group consisting of hydrogen, C₁-C₆-alkyl,        C₂-C₄-alkynyl, CH₂—CN, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl,        C₃-C₆-halocycloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;    -   and    -   each R¹⁶ as a substituent on phenyl or heterocyclic rings of        formulae E-1 to E-57 is independently selected from the group        consisting of halogen, cyano, nitro, C₁-C₄-alkyl,        C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,        C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfinyl,        C₁-C₄-haloalkylsulfinyl, C₁-C₄-alkylsulfonyl,        C₁-C₄-haloalkylsulfonyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,        C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl,        C₂-C₄-haloalkynyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl,        aminocarbonyl, C₁-C₄-alkylaminocarbonyl and        di-(C₁-C₄-alkyl)-aminocarbonyl; or        -   two R¹⁶ present on the same carbon atom of a saturated            heterocyclic ring may form together ═O or ═S; or        -   two R¹⁶ present on the same S or SO ring member of a            heterocyclic ring may together form a group ═N(C₁-C₆-alkyl),            ═NO(C₁-C₆-alkyl), ═NN(H)(C₁-C₆-alkyl) or ═NN(C₁-C₆-alkyl)₂.

In a preferred embodiment of embodiment 2a, R¹¹, in addition to theabove definitions, is also selected from C₃-C₆-cycloalkyl-C₁-C₄-alkyl.

In a particular embodiment of embodiment 2a (embodiment 2aa), R⁶, inaddition to the above definitions in embodiment 2a, is also selectedfrom rings F-58 to F-60

where k and R¹¹ are as defined for rings F-1 to F-57, where howeveradditionally, two R¹¹ present on the same carbon atom of a partiallyunsaturated heterocyclic ring (like ring F-59) may form together═O or═S;and R⁸, in addition to the above definitions in embodiment 2a, is alsoselected from C₃-C₈-cycloalkyl which optionally carries a CH F₂substituent, and from 1,3-dioxolan-2-yl which may carry 1, 2 or 3substituents R¹⁶ as defined above.

In a preferred embodiment of embodiment 2aa, R¹¹, in addition to theabove definitions, is also selected from C₃-C₆-cycloalkyl-C₁-C₄-alkyl.

In another preferred embodiment of embodiment 2 (embodiment 2b)

-   R⁵ is hydrogen or C₁-C₃-alkyl;-   R⁶ is selected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,    C₁-C₄-alkyl which carries one radical R⁸, wherein R⁸ is as defined    below; C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,    C₃-C₆-cycloalkyl which may be substituted by 1 or 2 substituents    selected from F, CN and pyridyl;    -   —N(R^(101a))R^(101b), wherein R^(101a) and R^(101b) are as        defined below;    -   —CH═NOR^(9a), wherein R^(9a) is selected from hydrogen,        C₁-C₆-alkyl and C₁-C₆-haloalkyl;    -   phenyl which may be substituted with 1, 2, 3, 4, or 5        substituents R¹¹, wherein R¹¹ is as defined below; and a        heteromonocyclic ring selected from rings of formulae F-1 to        F-57 as defined above;    -   where    -   in F-1 to F-57    -   the zigzag line denotes the attachment point to the remainder of        the molecule;    -   k is 0, 1, 2 or 3,    -   n is 0, 1 or 2, and    -   R¹¹ is as defined below;    -   R⁸ is selected from OH, CN, C₃-C₈-cycloalkyl which optionally        carries a CN or CF₃ substituent, C₃-C₈-halocycloalkyl,        C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,        C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,        C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,        C₁-C₆-haloalkylsulfonyl, —C(═O)N(R^(102a))R^(102b), phenyl,        optionally substituted with 1, 2, 3, 4 or 5 substituents R¹⁶,        and a heterocyclic ring selected from rings of formulae E-1 to        E-57 as defined above;        -   wherein        -   R^(102a) in —C(═O)N(R^(102a))R^(102b) as a meaning for R⁸ is            selected from the group consisting of hydrogen and            C₁-C₆-alkyl; and        -   R^(102b) in —C(═O)N(R^(102a))R^(102b) as a meaning for R⁸ is            selected from the group consisting of hydrogen, C₁-C₆-alkyl,            C₁-C₆-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,            C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,            C₃-C₆-cycloalkyl-methyl, CH₂—CN, C₁-C₆-alkoxy and            C₁-C₆-haloalkoxy;    -   R^(101a) in —N(R^(101a))R^(101b) as a meaning for R⁶ is selected        from hydrogen and C₁-C₆-alkyl; and    -   R^(101b) in —N(R^(101a))R^(101b) as a meaning for R⁶ is selected        from hydrogen, —C(═O)N(R^(14a))R^(14b), phenyl, optionally        substituted with 1, 2, 3, 4 or 5 substituents R¹⁶, wherein R¹⁶        is as defined below; and a heteroaromatic ring selected from        rings of formulae E-1 to E-42 as defined above;    -   each R¹¹ is independently selected from the group consisting of        halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl,        C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,        C₁-C₄-haloalkylthio, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,        C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl and        C₂-C₄-haloalkynyl; or two R¹¹ present on the same carbon atom of        a saturated heterocyclic ring may form together═O or ═S; or    -   two R¹¹ present on the same S or SO ring member of a        heterocyclic ring may together form a group ═N(C₁-C₆-alkyl),        ═NO(C₁-C₆-alkyl), ═NN(H)(C₁-C₆-alkyl) or ═NN(C₁-C₆-alkyl)₂;    -   R^(14a) in —C(═O)N(R^(14a))R^(14b) as a meaning for R^(102b) is        selected from the group consisting of hydrogen and C₁-C₆-alkyl;        and    -   R^(14b) in —C(═O)N(R^(14a))R^(14b) as a meaning for R^(102b) is        selected from the group consisting of hydrogen, C₁-C₆-alkyl,        C₂-C₄-alkynyl, CH₂—CN, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl,        C₃-C₆-halocycloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;    -   and    -   each R¹⁶ as a substituent on phenyl or heterocyclic rings of        formulae E-1 to E-57 is independently selected from the group        consisting of halogen, cyano, nitro, C₁-C₄-alkyl,        C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,        C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfinyl,        C₁-C₄-haloalkylsulfinyl, C₁-C₄-alkylsulfonyl,        C₁-C₄-haloalkylsulfonyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,        C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl,        C₂-C₄-haloalkynyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl,        aminocarbonyl, C₁-C₄-alkylaminocarbonyl and        di-(C₁-C₄-alkyl)-aminocarbonyl; or two R¹⁶ present on the same        carbon atom of a saturated heterocyclic ring may form together        ═O or ═S.

In a preferred embodiment of embodiment 2b, R¹¹, in addition to theabove definitions, is also selected from C₃-C₆-cycloalkyl-C₁-C₄-alkyl.

In a particular embodiment of embodiment 2b (embodiment 2bb), R⁶, inaddition to the above definitions in embodiment 2b, is also selectedfrom rings F-58 to F-60

where k and R¹¹ are as defined for rings F-1 to F-57, where howeveradditionally, two R¹¹ present on the same carbon atom of a partiallyunsaturated heterocyclic ring (like ring F-59) may form together ═O or═S;and R⁸, in addition to the above definitions in embodiment 2b, is alsoselected from C₃-C₈-cycloalkyl which optionally carries a CH F₂substituent, and from 1,3-dioxolan-2-yl which may carry 1, 2 or 3substituents R¹⁶ as defined above.

In a preferred embodiment of embodiment 2bb, R¹¹, in addition to theabove definitions, is also selected from C₃-C₆-cycloalkyl-C₁-C₄-alkyl.

In a particular embodiment of embodiment 2 (embodiment 2c),

-   R⁵ is hydrogen or C₁-C₃-alkyl, and in particular hydrogen;-   R⁶ is selected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,    C₁-C₄-alkyl which carries one radical R⁸, wherein R⁸ is as defined    below; C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl which may be    substituted by 1 cyano group;    -   —N(R^(101a))R^(101b), wherein R^(101a) and R^(101b) are as        defined below;    -   and a heteromonocyclic ring selected from rings of formulae F-1        to F-57 as defined above;    -   where in F-1 to F-57    -   the zigzag line denotes the attachment point to the remainder of        the molecule;    -   k is 0 or 1 preferably 0,    -   n is 0, 1 or 2, and    -   R¹¹ is as defined below;    -   R⁸ is selected from CN, C₃-C₈-cycloalkyl which optionally        carries a CN or CF₃ substituent, C₃-C₈-halocycloalkyl,        —C(═O)N(R^(102a))R^(102b), and a heterocyclic ring selected from        rings of formulae E-1 to E-57 as defined above;        -   wherein        -   R^(102a) in —C(═O)N(R^(102a))R^(102b) as a meaning for R⁸ is            selected from the group consisting of hydrogen and            C₁-C₆-alkyl; and        -   R^(102b) in —C(═O)N(R^(102a))R^(102b) as a meaning for R⁸ is            selected from the group consisting of hydrogen, C₁-C₆-alkyl,            C₁-C₆-haloalkyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl,            C₃-C₆-halocycloalkyl, CH₂—CN, C₁-C₆-alkoxy and            C₁-C₆-haloalkoxy;    -   R^(101a) in —N(R^(101a))R^(101b) as a meaning for R⁶ is selected        from hydrogen and C₁-C₆-alkyl;    -   R^(101b) in —N(R^(101a))R^(101b) as a meaning for R⁶ is selected        from hydrogen, and a heteroaromatic ring selected from rings of        formulae F-1 to F-42 as defined above;    -   each R¹¹ is independently selected from the group consisting of        halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl,        C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,        C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfinyl,        C₁-C₄-haloalkylsulfinyl, C₁-C₄-alkylsulfonyl,        C₁-C₄-haloalkylsulfonyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,        C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl,        C₂-C₄-haloalkynyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl,        aminocarbonyl, C₁-C₄-alkylaminocarbonyl and        di-(C₁-C₄-alkyl)-aminocarbonyl; or        -   two R¹¹ present on the same carbon atom of a saturated            heterocyclic ring may form together ═O or ═S; or        -   two R¹ present on the same S or SO ring member of a            heterocyclic ring may together form a group ═N(C₁-C₆-alkyl),            ═NO(C₁-C₆-alkyl), ═NN(H)(C₁-C₆-alkyl) or ═NN(C₁-C₆-alkyl)₂;    -   and    -   each R¹⁶ as a substituent on phenyl or heterocyclic rings of        formulae E-1 to E-57 is independently selected from the group        consisting of halogen, cyano, nitro, C₁-C₄-alkyl,        C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,        C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfinyl,        C₁-C₄-haloalkylsulfinyl, C₁-C₄-alkylsulfonyl,        C₁-C₄-haloalkylsulfonyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,        C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl,        C₂-C₄-haloalkynyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl,        aminocarbonyl, C₁-C₄-alkylaminocarbonyl and        di-(C₁-C₄-alkyl)-aminocarbonyl; or        -   two R¹⁶ present on the same carbon atom of a saturated            heterocyclic ring may form together ═O or ═S; or        -   two R¹⁶ present on the same S or SO ring member of a            heterocyclic ring may together form a group ═N(C₁-C₆-alkyl),            ═NO(C₁-C₆-alkyl), ═NN(H)(C₁-C₆-alkyl) or ═NN(C₁-C₆-alkyl)₂.

In a preferred embodiment of embodiment 2c, R¹¹, in addition to theabove definitions, is also selected from C₃-C₆-cycloalkyl-C₁-C₄-alkyl.

In a particular embodiment of embodiment 2c (embodiment 2cc), R⁶, inaddition to the above definitions in embodiment 2c, is also selectedfrom rings F-58 to F-60

where k and R¹¹ are as defined for rings F-1 to F-57, where howeveradditionally, two R¹¹ present on the same carbon atom of a partiallyunsaturated heterocyclic ring (like ring F-59) may form together ═O or═S;and R⁸, in addition to the above definitions in embodiment 2a, is alsoselected from C₃-C₈-cycloalkyl which optionally carries a CH F₂substituent, and from 1,3-dioxolan-2-yl which may carry 1, 2 or 3substituents R¹⁶ as defined above.

In a preferred embodiment of embodiment 2cc, R¹¹, in addition to theabove definitions, is also selected from C₃-C₆-cycloalkyl-C₁-C₄-alkyl.

In another even more particular embodiment of embodiment 2 (embodiment2d),

-   R⁵ is hydrogen or C₁-C₃-alkyl;-   R⁶ is selected from C₁-C₄-alkyl which carries one radical R⁸, and a    saturated heteromonocyclic ring selected from rings of formulae F-43    to F-57 as defined above; wherein    -   R⁸ is a saturated heterocyclic ring selected from rings of        formulae E-43 to E-57 as defined above;    -   R¹¹ as a substituent on heterocyclic rings of formulae F-43 to        F-57 is independently selected from the group consisting of        halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl,        C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,        C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfinyl,        C₁-C₄-haloalkylsulfinyl, C₁-C₄-alkylsulfonyl,        C₁-C₄-haloalkylsulfonyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,        C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl,        C₂-C₄-haloalkynyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl,        aminocarbonyl, C₁-C₄-alkylaminocarbonyl and        di-(C₁-C₄-alkyl)-aminocarbonyl; or two R¹¹ present on the same        carbon atom of a saturated heterocyclic ring may form together        ═O or ═S;    -   each R¹⁶ as a substituent on heterocyclic rings of formulae E-43        to E-57 is independently selected from the group consisting of        halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl,        C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,        C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfinyl,        C₁-C₄-haloalkylsulfinyl, C₁-C₄-alkylsulfonyl,        C₁-C₄-haloalkylsulfonyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,        C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl,        C₂-C₄-haloalkynyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl,        aminocarbonyl, C₁-C₄-alkylaminocarbonyl and        di-(C₁-C₄-alkyl)-aminocarbonyl; or two R¹⁶ present on the same        carbon atom of a saturated heterocyclic ring may form together        ═O or ═S.

In a preferred embodiment of embodiment 2d, R¹¹, in addition to theabove definitions, is also selected from C₃-C₆-cycloalkyl-C₁-C₄-alkyl.

In embodiment 2c, and also 2cc and also 2d, the heteromonocyclic ring R⁶is preferably selected from rings of formulae F-44-1 and F-53-1 (seebelow), and the heterocyclic ring R⁸ is preferably selected from ringsof formulae E-1, E-2, E-3, E-5, E-7, E-44-1 and E-57-1 (see below),specifically from E-1, E-7, E-44-1 and E-57-1 and very specifically fromE-44-1 and E-57-1.

In embodiments 2, 2a, 2aa, 2b, 2bb, 2c, 2cc and 2d, the heteromonocyclicring R⁶ is preferably selected from rings of formulae F-44-1 and F-53-1,and the heterocyclic ring R⁸ is preferably selected from rings offormulae E-44-1 and E-57-1

wherein

-   n is 0, 1 or 2; and-   R¹⁷ is selected from the group consisting of hydrogen, C₁-C₄-alkyl,    C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,    C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl    and CH₂—C₃-C₆-cycloalkyl.

In an especially preferred embodiment of embodiment 2 (embodiment 2e)

-   R⁵ is hydrogen or C₁-C₃-alkyl, in particular hydrogen; and-   R⁶ is selected from C₁-C₄-alkyl (especially methyl) which carries    one radical R⁸; a ring of formula F-44-1, and a ring of formula    F-53-1 as defined above; wherein    -   R⁸ is selected from a ring of formula E-44-1 and a ring of        formula E-57-1 as defined above.

In another preferred embodiment of embodiment 2 (embodiment 2f), R⁵ andR⁶ together form a group ═S(R^(9b))₂, where R^(9b) is selected fromC₁-C₄-alkyl and C₁-C₂-haloalkyl and in particular from C₁-C₄-alkyl.

In another preferred embodiment of embodiment 2 (embodiment 2g), R⁵ andR⁶, together with the nitrogen atom to which they are bound, form a5-membered saturated heterocyclic ring, where the ring may furthercontain 1 or 2 heteroatoms or heteroatom-containing groups selected fromNH and C═O as ring members, wherein the heterocyclic ring may besubstituted with 1, 2 or 3 substituents independently selected fromC₁-C₆-alkyl and C₁-C₆-haloalkyl. In a particular embodiment ofembodiment 2g (embodiment 2gg), R⁵ and R⁶, together with the nitrogenatom to which they are bound, form an imidazolidinon-1-yl ring,especially an imidazolidin-4-on-1-yl ring which may be substituted with1 or 2 substituents independently selected from C₁-C₆-alkyl andC₁-C₆-haloalkyl.

Preferably, B¹ is CR², where R² is not hydrogen, and B² and B³ are CR²,where R² has one of the above general, or, on particular, one of thebelow preferred meanings. In a particular embodiment (embodiment 3a), incompounds I, B¹ is CR², where R² is not hydrogen, and B² and B³ are CR²,where R² has one of the above general or, in particular, one of thebelow preferred meanings; W is O; and Y is as defined in any of theabove embodiments 1a, 2a, 2aa, 2b, 2bb, 2c, 2cc, 2d, 2e, 2f, 2g or 2gg.

Preferably, R² is selected from hydrogen, F, Cl, Br, OCF₃ and CF₃; andis specifically F or Cl.

In a particular embodiment (embodiment 3b), in compounds I, B¹ is CR²,where R² is not hydrogen, and B² and B³ are CR², where R² is selectedfrom hydrogen, F, Cl, Br, OCF₃ and CF₃; and is specifically F or Cl; Wis O; and Y is as defined in any of the above embodiments 1a, 2a, 2aa,2b, 2bb, 2c, 2cc, 2d, 2e, 2f, 2g or 2gg.

Preferably, G¹ and G² are CR⁴, where R⁴ has one of the above general or,in particular, one of the below preferred meanings.

R⁴ is in particular hydrogen.

In a particular embodiment (embodiment 4a), in compounds I, R⁴ has oneof the above general or, in particular, one of the below preferredmeanings, and is in particular hydrogen; B¹, B² and B³ are as defined inembodiments 3a or 3b, W is O; and Y is as defined in any of the aboveembodiments 1a, 2a, 2aa, 2b, 2bb, 2c, 2cc, 2d, 2e, 2f, 2g or 2gg.

In one embodiment, R^(g1) and R^(g2) form together a bridging group—CH₂—CH₂—CH₂—.

In another embodiment, R^(g1) and R^(g2) form together a bridging group—CH₂—CH₂—CH₂—CH₂—.

Preferably, R^(3a) and R^(3b) are independently selected from hydrogenand halogen, more preferably from hydrogen and fluorine, and are inparticular hydrogen.

In a particular embodiment (embodiment 5a), in compounds I, R^(3a) andR^(3b) are hydrogen, R⁴ is as defined in embodiment 4a; B¹, B² and B³are as defined in embodiments 3a or 3b, W is O; and Y is as defined inany of the above embodiments 1a, 2a, 2aa, 2b, 2bb, 2c, 2cc, 2d, 2e, 2f,2g or 2gg.

If not specified otherwise above, R¹⁶ has following preferred meanings:

R¹⁶ is independently of each occurrence and independently of each otherpreferably selected from halogen, CN, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio,C₁-C₄-alkylsulfinyl, C₁-C₄-haloalkylsulfinyl, C₁-C₄-alkylsulfonyl andC₁-C₄-haloalkylsulfonyl, and more preferably from halogen, CN,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy. Ifbound to a nitrogen atom, R¹⁶ is not halogen.

In a particular embodiment, the compound of formula I is a compound offormula IA or an N-oxide, a stereoisomer or an agriculturally orveterinarily acceptable salt thereof

wherein

-   X¹ is O of CH₂;-   R^(2a), R^(2b) and R^(2c) have one of the above general or, in    particular, on of the above preferred meanings of R²;-   A has one of the above general or, in particular, on of the above    preferred meanings; and-   a is 1 or 2.

In particular, in compounds IA, in A, W is O and Y is as defined in anyof embodiments 1a, 2a, 2aa, 2b, 2bb, 2c, 2cc, 2d, 2e, 2f, 2g or 2gg, andespecially 2c, 2cc, 2d or 2e.

In a more particular embodiment, the compound of formula I is a compoundof formula IB or a stereoisomer or an agriculturally or veterinarilyacceptable salt thereof

wherein

-   R^(2a) is Cl, R^(2b) is F, R^(2c) is Cl, and-   R⁶ is CH₂—C(O)—N(H)—R^(102b), wherein    -   R^(102b) is selected from the group consisting of C₁-C₄-alkyl,        C₂-C₄-alkyl substituted with 1 or 2 fluorine atoms,        C₂-C₄-alkenyl, C₂-C₄-alkynyl, CH₂—CN, C₃-C₆-cycloalkyl,        C₃-C₆-halocycloalkyl and C₃-C₆-cycloalkylmethyl.

In another more particular embodiment, the compound of formula I is acompound of formula IB, as defined above, or a stereoisomer or anagriculturally or veterinarily acceptable salt thereof, where however

-   R^(2a) is Cl, R^(2b) is F, R^(2c) is Cl, and-   R⁶ is —CH₂—R⁸, wherein    -   R⁸ is selected from rings E-5, E-6, E-7, E-19, E-25, E-27, E-44        and E-57 as defined above, where the rings E-5, E-6, E-7, E-19,        E-27, E-44 and E-57 are unsubstituted (k is O) or carry 1 or 2        substituents R¹⁶ (k is 1 or 2); and is in particular selected        from rings E-5, E-6, E-7, E-19, E-25, E-27, E-44-1 and E-57-1,        where the rings E-5, E-6, E-7, E-19 and E-27 are unsubstituted        (k is 0) or carry 1 or 2 substituents R¹⁶ (k is 1 or 2),        -   wherein        -   each R¹⁶ is independently selected from halogen, cyano,            nitro, C₁-C₂-alkyl, C₁-C₂-haloalkyl, C₁-C₂-alkoxy,            C₁-C₂-haloalkoxy, C₁-C₂-alkylthio, C₁-C₂-haloalkylthio,            C₁-C₂-alkylsulfinyl, C₁-C₂-haloalkylsulfinyl,            C₁-C₂-alkylsulfonyl, C₁-C₂-haloalkylsulfonyl,            C₃-C₄-cycloalkyl, C₃-C₄-halocycloalkyl, C₂-C₃-alkenyl,            C₂-C₃-alkynyl; and        -   where ring E-25 carries one substituent R¹⁶ as defined above            on the nitrogen atom in the 1-position (which is however not            halogen, cyano, nitro, C₁-C₂-alkoxy, C₁-C₂-haloalkoxy,            C₁-C₂-alkylthio, C₁-C₂-haloalkylthio, C₁-C₂-alkylsulfinyl,            C₁-C₂-haloalkylsulfinyl, C₁-C₂-alkylsulfonyl or            C₁-C₂-haloalkylsulfonyl) and optionally carries 1 or 2            further substituents R¹⁶, where R¹⁶ is as defined above.

In yet another more particular embodiment, the compound of formula I isa compound of formula IB, as defined above, or a stereoisomer or anagriculturally or veterinarily acceptable salt thereof, where however

-   R^(2a) is Cl, R^(2b) is F, R^(2c) is Cl, and-   R⁶ is selected from rings F-2, F-4, F-6, F-8, F-9, F-44, F-46, F-51    and F-53 as defined above, where the rings F-2, F-4, F-6, F-8, F-9,    F-44, F-46 and F-53 are unsubstituted (k is 0) or carry 1 or 2    substituents R¹¹ (k is 1 or 2),    wherein    -   each R¹¹ is independently selected from halogen, cyano, nitro,        C₁-C₂-alkyl, C₁-C₂-haloalkyl, C₁-C₂-alkoxy, C₁-C₂-haloalkoxy,        C₁-C₂-alkylthio, C₁-C₂-haloalkylthio, C₁-C₂-alkylsulfinyl,        C₁-C₂-haloalkylsulfinyl, C₁-C₂-alkylsulfonyl,        C₁-C₂-haloalkylsulfonyl, C₃-C₄-cycloalkyl, C₃-C₄-halocycloalkyl,        C₂-C₃-alkenyl and C₂-C₃-alkynyl; and    -   where ring F-51 is a ring of formula F-51-1

-   -   -   wherein        -   R¹⁸ is selected from the group consisting of hydrogen,            C₁-C₂-alkyl, C₁-C₂-haloalkyl, C₃-C₄-cycloalkyl,            C₃-C₄-halocycloalkyl, C₂-C₃-alkenyl and C₂-C₃-alkynyl;

    -   and

    -   where rings F-44 and F-53 are preferably rings F-44-1 and F-53-1        as defined above.

In yet another more particular embodiment, the compound of formula I isa compound of formula IB, as defined above, or a stereoisomer or anagriculturally or veterinarily acceptable salt thereof, where however

-   R^(2a) is Cl, R^(2b) is F, R^(2c) is Cl, and-   R⁶ is selected from C₂-C₄-alkyl which may be substituted with 1 or 2    fluorine atoms, cyclopropyl, C₃-C₅-halocycloalkyl,    CH₂—(C₃-C₅-halocycloalkyl), CH₂-(1-cyano-(C₃-C₅-cycloalkyl)),    C₂-C₄-alkenyl, C₂-C₄-alkynyl, CH₂—CN and —CH═NOR^(9a), wherein    R^(9a) is selected from C₁-C₃-alkyl and C₁-C₃-haloalkyl.

In yet another more particular embodiment, the compound of formula I isa compound of formula IB, as defined above, or a stereoisomer or anagriculturally or veterinarily acceptable salt thereof, where however

-   R^(2a) is Cl, R^(2b) is F, R^(2c) is Cl, and-   R⁶ is N(H)R^(101b), wherein    -   R^(101b) is selected from —C(O)—N(H)R^(14b) and rings E-1 and        E-7 as defined above;        -   where        -   R^(14b) is selected from C₁-C₃-alkyl, C₁-C₃-haloalkyl and            cyclopropyl; and        -   where in rings E-1 and E-7        -   k is 0, 1 or 2; and        -   each R¹⁶ is independently selected from halogen, cyano,            nitro, C₁-C₂-alkyl, C₁-C₂-haloalkyl, C₁-C₂-alkoxy,            C₁-C₂-haloalkoxy, C₁-C₂-alkylthio, C₁-C₂-haloalkylthio,            C₁-C₂-alkylsulfinyl, C₁-C₂-haloalkylsulfinyl,            C₁-C₂-alkylsulfonyl, C₁-C₂-haloalkylsulfonyl,            C₃-C₄-cycloalkyl, C₃-C₄-halocycloalkyl, C₂-C₃-alkenyl,            C₂-C₃-alkynyl.

In another more particular embodiment, the compound of formula I is acompound of formula IB, as defined above, or a stereoisomer or anagriculturally or veterinarily acceptable salt thereof, where however

-   R^(2a) is Cl, R^(2b) is H, R^(2c) is Cl, and-   R⁶ is CH₂—C(O)—N(H)—R^(102b), wherein-   R^(102b) is selected from the group consisting of 2,2-difluoroethyl,    2,2,2-trifluoroethyl, cyclopropyl, cyclopropylmethyl, allyl and    propargyl.

In another more particular embodiment, the compound of formula I is acompound of formula IB, as defined above, or a stereoisomer or anagriculturally or veterinarily acceptable salt thereof, where however

-   R^(2a) is Cl, R^(2b) is H, R^(2c) is Cl, and-   R⁶ is —CH₂—R⁸, wherein    -   R⁸ is selected from following rings: E-1, E-7, E-19, E-44, E-47        and E-57, where in rings E-1, E-7, E-19, E-44, E-47 and E-57 k        is 0.

In another more particular embodiment, the compound of formula I is acompound of formula IB, as defined above, or a stereoisomer or anagriculturally or veterinarily acceptable salt thereof, where however

-   R^(2a) is Cl, R^(2b) is H, R^(2c) is Cl, and-   R⁶ is selected from rings F-9, F-44, F-46 and F-53; where in rings    F-9, F-44 and F-46 k is 0; and is in particular selected from rings    F-9, F-44, F-46 and F-53-1 with R¹⁷═H, methyl, ethyl or    2,2,2-trifluoroethyl; where in rings F-9, F-44 and F-46 k is 0.

In another more particular embodiment, the compound of formula I is acompound of formula IB, as defined above, or a stereoisomer or anagriculturally or veterinarily acceptable salt thereof, where however

-   R^(2a) is Cl, R^(2b) is H, R^(2C) is Cl, and-   R⁶ is selected from 2,2-difluoroethyl, 2,2,2-trifluoroethyl,    cyclopropyl, 2,2-difluorocyclopropyl, 1-cyanocyclopropyl,    cyclobutyl, 3,3-difluorocyclobutyl, cyclopropylmethyl,    2,2-difluorocyclopropylmethyl, 1-cyanocyclopropylmethyl,    cyclobutylmethyl, 3,3-difluorocyclobutylmethyl, allyl, propargyl and    —CH═NOCH₃.

In another more particular embodiment, the compound of formula I is acompound of formula IB, as defined above, or a stereoisomer or anagriculturally or veterinarily acceptable salt thereof, where however

-   R^(2a) is Cl, R^(2b) is H, R^(2c) is Cl, and-   R⁶ is N(H)R^(101b), wherein    -   R^(101b) is selected from —C(O)—N(H)—CH₂CF₃ and rings E-1 and        E-7, where in rings E-1 and E-7 k is 0.

In another more particular embodiment, the compound of formula I is acompound of formula IC or an N-oxide, a stereoisomer or anagriculturally or veterinarily acceptable salt thereof

wherein

-   R^(2a) is Cl, R^(2b) is F, R^(2c) is Cl, and-   R⁶ is CH₂—C(O)—N(H)—R^(102b), wherein-   R^(102b) is selected from the group consisting of 2,2-difluoroethyl,    2,2,2-trifluoroethyl, cyclopropyl, cyclopropylmethyl, allyl and    propargyl.

In another more particular embodiment, the compound of formula I is acompound of formula IC, as defined above, or an N-oxide, a stereoisomeror an agriculturally or veterinarily acceptable salt thereof, wherehowever

-   R^(2a) is Cl, R^(2b) is F, R^(2c) is Cl, and-   R⁶ is —CH₂—R⁸, wherein    -   R⁸ is selected from following rings: E-1, E-7, E-19, E-44, E-47        and E-57, where in rings E-1, E-7, E-19, E-44, E-47 and E-57 k        is 0.

In another more particular embodiment, the compound of formula I is acompound of formula IC, as defined above, or an N-oxide, a stereoisomeror an agriculturally or veterinarily acceptable salt thereof, wherehowever

-   R^(2a) is Cl, R^(2b) is F, R^(2c) is Cl, and-   R⁶ is selected from rings F-9, F-44, F-46 and F-53, where in rings    F-9, F-44 and F-46 k is 0, and is in particular selected from rings    F-9, F-44, F-46 and F-53-1 with R¹⁷═H, methyl, ethyl or    2,2,2-trifluoroethyl; where in rings F-9, F-44 and F-46 k is 0.

In another more particular embodiment, the compound of formula I is acompound of formula IC, as defined above, or an N-oxide, a stereoisomeror an agriculturally or veterinarily acceptable salt thereof, wherehowever

-   R^(2a) is Cl, R^(2b) is F, R^(2c) is Cl, and-   R⁶ is selected from 2,2-difluoroethyl, 2,2,2-trifluoroethyl,    cyclopropyl, 2,2-difluorocyclopropyl, 1-cyanocyclopropyl,    cyclobutyl, 3,3-difluorocyclobutyl, cyclopropylmethyl,    2,2-difluorocyclopropylmethyl, 1-cyanocyclopropylmethyl,    cyclobutylmethyl, 3,3-difluorocyclobutylmethyl, allyl, propargyl and    —CH═NOCH₃.

In another more particular embodiment, the compound of formula I is acompound of formula IC, as defined above, or an N-oxide, a stereoisomeror an agriculturally or veterinarily acceptable salt thereof, wherehowever

-   R^(2a) is Cl, R^(2b) is F, R^(2c) is Cl, and-   R⁶ is N(H)R^(101b), wherein    -   R^(101b) is selected from —C(O)—N(H)—CH₂CF₃ and rings E-1 and        E-7, where in rings E-1 and E-7 k is 0.

In another more particular embodiment, the compound of formula I is acompound of formula IC, as defined above, or an N-oxide, a stereoisomeror an agriculturally or veterinarily acceptable salt thereof, wherehowever

-   R^(2a) is Cl, R^(2b) is H, R^(2c) is Cl, and-   R⁶ is CH₂—C(O)—N(H)—R^(102b), wherein-   R^(102b) is selected from the group consisting of 2,2-difluoroethyl,    2,2,2-trifluoroethyl, cyclopropyl, cyclopropylmethyl, allyl and    propargyl.

In another more particular embodiment, the compound of formula I is acompound of formula IC, as defined above, or an N-oxide, a stereoisomeror an agriculturally or veterinarily acceptable salt thereof, wherehowever

-   R^(2a) is Cl, R^(2b) is H, R^(2c) is Cl, and-   R⁶ is —CH₂—R⁸, wherein    -   R⁸ is selected from following rings: E-1, E-7, E-19, E-44, E-47        and E-57, where in rings E-1, E-7, E-19, E-44, E-47 and E-57 k        is 0.

In another more particular embodiment, the compound of formula I is acompound of formula IC, as defined above, or an N-oxide, a stereoisomeror an agriculturally or veterinarily acceptable salt thereof, wherehowever

-   R^(2a) is Cl, R^(2b) is H, R^(2c) is Cl, and-   R⁶ is selected from rings F-9, F-44, F-46 and F-53, where in rings    F-9, F-44 and F-46 k is 0, and is in particular selected from rings    F-9, F-44, F-46 and F-53-1 with R¹⁷═H, methyl, ethyl or    2,2,2-trifluoroethyl; where in rings F-9, F-44 and F-46 k is 0.

In another more particular embodiment, the compound of formula I is acompound of formula IC, as defined above, or an N-oxide, a stereoisomeror an agriculturally or veterinarily acceptable salt thereof, wherehowever

-   R^(2a) is Cl, R^(2b) is H, R^(2c) is Cl, and-   R⁶ is selected from 2,2-difluoroethyl, 2,2,2-trifluoroethyl,    cyclopropyl, 2,2-difluorocyclopropyl, 1-cyanocyclopropyl,    cyclobutyl, 3,3-difluorocyclobutyl, cyclopropylmethyl,    2,2-difluorocyclopropylmethyl, 1-cyanocyclopropylmethyl,    cyclobutylmethyl, 3,3-difluorocyclobutylmethyl, allyl, propargyl and    —CH═NOCH₃.

In another more particular embodiment, the compound of formula I is acompound of formula IC, as defined above, or an N-oxide, a stereoisomeror an agriculturally or veterinarily acceptable salt thereof, wherehowever

-   R^(2a) is Cl, R^(2b) is H, R^(2c) is Cl, and-   R⁶ is N(H)R^(101b), wherein    -   R^(101b) is selected from —C(O)—N(H)—CH₂CF₃ and rings E-1 and        E-7, where in rings E-1 and E-7 k is 0.

Examples of preferred compounds are compounds of the following formulaeIa.1 to Ia.4, where R^(2a), R^(2b) and R^(2c) have one of the general orpreferred meanings given above for R² and the other variables have oneof the general or preferred meanings given above. Examples of preferredcompounds are the individual compounds compiled in the tables 1 to 7292below. Moreover, the meanings mentioned below for the individualvariables in the tables are per se, independently of the combination inwhich they are mentioned, a particularly preferred embodiment of thesubstituents in question.

Table 1

Compounds of the formula Ia.1 in which R⁶ is hydrogen, R⁵ is hydrogen,and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 2

Compounds of the formula Ia.1 in which R⁶ is —CN, R⁵ is hydrogen, andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 3

Compounds of the formula Ia.1 in which R⁶ is methyl, R⁵ is hydrogen, andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 4

Compounds of the formula Ia.1 in which R⁶ is ethyl, R⁵ is hydrogen, andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 5

Compounds of the formula Ia.1 in which R⁶ is n-propyl, R⁵ is hydrogen,and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 6

Compounds of the formula Ia.1 in which R⁶ is isopropyl, R⁵ is hydrogen,and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 7

Compounds of the formula Ia.1 in which R⁶ is n-butyl, R⁵ is hydrogen,and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 8

Compounds of the formula Ia.1 in which R⁶ is sec-butyl, R⁵ is hydrogen,and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 9

Compounds of the formula Ia.1 in which R⁶ is isobutyl, R⁵ is hydrogen,and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 10

Compounds of the formula Ia.1 in which R⁶ is tert-butyl, R⁵ is hydrogen,and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 11

Compounds of the formula Ia.1 in which R⁶ is CH₂—C(CH₃)₃, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 12

Compounds of the formula Ia.1 in which R⁶ is —CH₂CN, R⁵ is hydrogen, andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 13

Compounds of the formula Ia.1 in which R⁶ is —CH═CH₂, R⁵ is hydrogen,and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 14

Compounds of the formula Ia.1 in which R⁶ is —CH₂—CH═CH₂, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 15

Compounds of the formula Ia.1 in which R⁶ is —CH₂—CH₂—CH═CH₂, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 16

Compounds of the formula Ia.1 in which R⁶ is —CH₂—CH═CH—CH₃, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 17

Compounds of the formula Ia.1 in which R⁶ is —CH₂—CCl═CCl₂, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 18

Compounds of the formula Ia.1 in which R⁶ is —C≡CH, R⁵ is hydrogen, andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 19

Compounds of the formula Ia.1 in which R⁶ is —CH₂C≡CH, R⁵ is hydrogen,and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 20

Compounds of the formula Ia.1 in which R⁶ is —CH₂CH₂C≡CH, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 21

Compounds of the formula Ia.1 in which R⁶ is —CH₂CH₂OH, R⁵ is hydrogen,and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 22

Compounds of the formula Ia.1 in which R⁶ is —CH₂CH₂OCH₃, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 23

Compounds of the formula Ia.1 in which R⁶ is —CH₂CH₂OCH₂CH₃, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 24

Compounds of the formula Ia.1 in which R⁶ is —CH₂CH₂OCH₂CH═CH₂, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 25

Compounds of the formula Ia.1 in which R⁶ is —CH₂CH₂OCH₂C≡CH, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 26

Compounds of the formula Ia.1 in which R⁶ is —CH₂CH₂OCH₂-cyclopropyl, R⁵is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 27

Compounds of the formula Ia.1 in which R⁶ is —CH₂CH₂OCF₃, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 28

Compounds of the formula Ia.1 in which R⁶ is —CH₂CH₂OCH₂CF₃, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 29

Compounds of the formula Ia.1 in which R⁶ is —CH₂CH₂SCH₃, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 30

Compounds of the formula Ia.1 in which R⁶ is —CH₂CH₂S(O)CH₃, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 31

Compounds of the formula Ia.1 in which R⁶ is —CH₂CH₂S(O)₂CH₃, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 32

Compounds of the formula Ia.1 in which R⁶ is —CH₂CH₂SCH₂CH₃, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 33

Compounds of the formula Ia.1 in which R⁶ is —CH₂CH₂S(O)CH₂CH₃, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 34

Compounds of the formula Ia.1 in which R⁶ is —CH₂CH₂S(O)₂CH₂CH₃, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 35

Compounds of the formula Ia.1 in which R⁶ is —CH₂CH₂S(O)₂CH₂CH═CH₂, R⁵is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 36

Compounds of the formula Ia.1 in which R⁶ is —CH₂CH₂S(O)₂CH₂C≡CH, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 37

Compounds of the formula Ia.1 in which R⁶ is—CH₂CH₂S(O)₂CH₂-cyclopropyl, R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 38

Compounds of the formula Ia.1 in which R⁶ is —CH₂CH₂SCF₃, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 39

Compounds of the formula Ia.1 in which R⁶ is —CH₂CH₂S(O)CF₃, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 40

Compounds of the formula Ia.1 in which R⁶ is CH₂CH₂F, R⁵ is hydrogen,and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 41

Compounds of the formula Ia.1 in which R⁶ is CH₂CH F₂, R⁵ is hydrogen,and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 42

Compounds of the formula Ia.1 in which R⁶ is CH₂CF₃, R⁵ is hydrogen, andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 43

Compounds of the formula Ia.1 in which R⁶ is CH₂CH₂CH F₂, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 44

Compounds of the formula Ia.1 in which R⁶ is CH₂CH₂CF₃, R⁵ is hydrogen,and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 45

Compounds of the formula Ia.1 in which R⁶ is CH(CH₃)CF₃, R⁵ is hydrogen,and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 46

Compounds of the formula Ia.1 in which R⁶ is CH(CF₃)₂, R⁵ is hydrogen,and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 47

Compounds of the formula Ia.1 in which R⁶ is CH₂CH₂CH₂CF₃, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 48

Compounds of the formula Ia.1 in which R⁶ is cyclopropyl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 49

Compounds of the formula Ia.1 in which R⁶ is 1-cyano-cyclopropyl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 50

Compounds of the formula Ia.1 in which R⁶ is1-(pyridin-2-yl)-cyclopropyl, R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 51

Compounds of the formula Ia.1 in which R⁶ is 2,2-difluoro-cyclopropyl,R⁵ is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 52

Compounds of the formula Ia.1 in which R⁶ is cyclobutyl, R⁵ is hydrogen,and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 53

Compounds of the formula Ia.1 in which R⁶ is 1-cyano-cyclobutyl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 54

Compounds of the formula Ia.1 in which R⁶ is 3,3-difluorocyclobutyl, R⁵is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 55

Compounds of the formula Ia.1 in which R⁶ is cyclopentyl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 56

Compounds of the formula Ia.1 in which R⁶ is 1-cyano-cyclopentyl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 57

Compounds of the formula Ia.1 in which R⁶ is cyclohexyl, R⁵ is hydrogen,and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 58

Compounds of the formula Ia.1 in which R⁶ is 1-cyano-cyclohexyl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 59

Compounds of the formula Ia.1 in which R⁶ is —CH₂-cyclopropyl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 60

Compounds of the formula Ia.1 in which R⁶ is —CH₂-(1-cyano-cyclopropyl),R⁵ is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 61

Compounds of the formula Ia.1 in which R⁶ is—CH₂-(1-fluoro-cyclopropyl), R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 62

Compounds of the formula Ia.1 in which R⁶ is—CH₂-(1-chloro-cyclopropyl), R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 63

Compounds of the formula Ia.1 in which R⁶ is —CH₂-(1-bromo-cyclopropyl),R⁵ is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 64

Compounds of the formula Ia.1 in which R⁶ is—CH₂-(2,2-difluorocyclopropyl), R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 65

Compounds of the formula Ia.1 in which R⁶ is—CH₂-(2,2-dichlorocyclopropyl), R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 66

Compounds of the formula Ia.1 in which R⁶ is—CH₂-(2,2-dibromocyclopropyl), R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 67

Compounds of the formula Ia.1 in which R⁶ is—CH₂-(1-(difluoromethyl)-cyclopropyl), R⁵ is hydrogen, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 68

Compounds of the formula Ia.1 in which R⁶ is—CH₂-(1-(trifluoromethyl)-cyclopropyl), R⁵ is hydrogen, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 69

Compounds of the formula Ia.1 in which R⁶ is —CH₂-cyclobutyl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 70

Compounds of the formula Ia.1 in which R⁶ is —CH₂-(1-cyano-cyclobutyl),R⁵ is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 71

Compounds of the formula Ia.1 in which R⁶ is —CH₂-(1-fluoro-cyclobutyl),R⁵ is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 72

Compounds of the formula Ia.1 in which R⁶ is —CH₂-(1-chloro-cyclobutyl),R⁵ is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 73

Compounds of the formula Ia.1 in which R⁶ is—CH₂-(2,2-difluorocyclobutyl), R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 74

Compounds of the formula Ia.1 in which R⁶ is—CH₂-(3,3-difluorocyclobutyl), R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 75

Compounds of the formula Ia.1 in which R⁶ is is—CH₂-(2,2,3,3-tetrafluorocyclobutyl), R⁵ is hydrogen, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 76

Compounds of the formula Ia.1 in which R⁶ is—CH₂-(2,2,3,3,4,4-hexafluorocyclobutyl), R⁵ is hydrogen, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 77

Compounds of the formula Ia.1 in which R⁶ is —CH₂-cyclopentyl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 78

Compounds of the formula Ia.1 in which R⁶ is—CH₂-(-1-fluoro-cyclopentyl), R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 79

Compounds of the formula Ia.1 in which R⁶ is is—CH₂-(1-chloro-cyclopentyl), R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 80

Compounds of the formula Ia.1 in which R⁶ is —CH₂-(1-cyano-cyclopentyl),R⁵ is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 81

Compounds of the formula Ia.1 in which R⁶ is—CH₂-(2,2-difluorocyclopentyl), R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 82

Compounds of the formula Ia.1 in which R⁶ is—CH₂-(3,3-difluorocyclopentyl), R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 83

Compounds of the formula Ia.1 in which R⁶ is —CH₂-cyclohexyl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 84

Compounds of the formula Ia.1 in which R⁶ is —CH₂-(1-fluorocyclohexyl),R⁵ is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 85

Compounds of the formula Ia.1 in which R⁶ is —CH₂-(1-chlorocyclohexyl),R⁵ is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 86

Compounds of the formula Ia.1 in which R⁶ is —CH₂-(1-cyanocyclohexyl),R⁵ is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 87

Compounds of the formula Ia.1 in which R⁶ is thietan-3-yl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 88

Compounds of the formula Ia.1 in which R⁶ is 1-oxo-thietan-3-yl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 89

Compounds of the formula Ia.1 in which R⁶ is 1,1-dioxo-thietan-3-yl, R⁵is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 90

Compounds of the formula Ia.1 in which R⁶ is 3-methyl-thietan-3-yl, R⁵is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 91

Compounds of the formula Ia.1 in which R⁶ is 2,2-dimethyl-thietan-3-yl,R⁵ is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 92

Compounds of the formula Ia.1 in which R⁶ is3-methyl-1-oxo-thietan-3-yl, R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 93

Compounds of the formula Ia.1 in which R⁶ is2,2-dimethyl-1-oxo-thietan-3-yl, R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 94

Compounds of the formula Ia.1 in which R⁶ is3-methyl-1,1-dioxo-thietan-3-yl, R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 95

Compounds of the formula Ia.1 in which R⁶ is2,2-dimethyl-1,1-dioxo-thietan-3-yl, R⁵ is hydrogen, and the combinationof R^(2a), R^(2b) and R^(2c) for a compound corresponds in each case toone row of Table A

Table 96

Compounds of the formula Ia.1 in which R⁶ is —CH₂-thietan-3-yl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 97

Compounds of the formula Ia.1 in which R⁶ is —CH₂-(1-oxo-thietan-3-yl),R⁵ is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 98

Compounds of the formula Ia.1 in which R⁶ is—CH₂-(1,1-dioxo-thietan-3-yl), R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 99

Compounds of the formula Ia.1 in which R⁶ is —CH₂-thietan-2-yl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 100

Compounds of the formula Ia.1 in which R⁶ is —CH₂-(1-oxo-thietan-2-yl),R⁵ is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 101

Compounds of the formula Ia.1 in which R⁶ is—CH₂-(1,1-dioxo-thietan-2-yl), R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 102

Compounds of the formula Ia.1 in which R⁶ is tetrahydrothiophen-3-yl, R⁵is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 103

Compounds of the formula Ia.1 in which R⁶ is1-oxo-tetrahydrothiophen-3-yl, R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 104

Compounds of the formula Ia.1 in which R⁶ is1,1-dioxo-tetrahydrothiophen-3-yl, R⁵ is hydrogen, and the combinationof R^(2a), R^(2b) and R^(2c) for a compound corresponds in each case toone row of Table A

Table 105

Compounds of the formula Ia.1 in which R⁶ is phenyl, R⁵ is hydrogen, andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 106

Compounds of the formula Ia.1 in which R⁶ is 2-fluorophenyl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 107

Compounds of the formula Ia.1 in which R⁶ is pyridin-2-yl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 108

Compounds of the formula Ia.1 in which R⁶ is pyridin-3-yl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 109

Compounds of the formula Ia.1 in which R⁶ is pyridin-4-yl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 110

Compounds of the formula Ia.1 in which R⁶ is pyrimidin-2-yl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 111

Compounds of the formula Ia.1 in which R⁶ is pyrimidin-4-yl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 112

Compounds of the formula Ia.1 in which R⁶ is pyrimidin-5-yl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 113

Compounds of the formula Ia.1 in which R⁶ is pyrazin-2-yl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 114

Compounds of the formula Ia.1 in which R⁶ is pyridazin-3-yl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 115

Compounds of the formula Ia.1 in which R⁶ is pyridazin-4-yl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 116

Compounds of the formula Ia.1 in which R⁶ is pyrazol-3-yl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 117

Compounds of the formula Ia.1 in which R⁶ is 1-methylpyrazol-3-yl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 118

Compounds of the formula Ia.1 in which R⁶ is thiazol-2-yl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 119

Compounds of the formula Ia.1 in which R⁶ is 3-methylisothiazol-5-yl, R⁵is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 120

Compounds of the formula Ia.1 in which R⁶ is oxetan-3-yl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 121

Compounds of the formula Ia.1 in which R⁶ is tetrahydrofuran-2-yl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 122

Compounds of the formula Ia.1 in which R⁶ is tetrahydrofuran-3-yl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 123

Compounds of the formula Ia.1 in which R⁶ is 2-oxotetrahydrofuran-3-yl,R⁵ is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 124

Compounds of the formula Ia.1 in which R⁶ is 1-ethyl-pyrrolidin-3-yl, R⁵is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 125

Compounds of the formula Ia.1 in which R⁶ is 2-oxopyrrolidin-3-yl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 126

Compounds of the formula Ia.1 in which R⁶ is1-methyl-2-oxopyrrolidin-3-yl, R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 127

Compounds of the formula Ia.1 in which R⁶ is1-ethyl-2-oxopyrrolidin-3-yl, R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 128

Compounds of the formula Ia.1 in which R⁶ is2-oxo-1-(2,2,2-trifluoroethyl)-pyrrolidin-3-yl, R⁵ is hydrogen, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 129

Compounds of the formula Ia.1 in which R⁶ is 3-oxo-isoxazolidin-4-yl, R⁵is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 130

Compounds of the formula Ia.1 in which R⁶ is2-methyl-3-oxo-isoxazolidin-4-yl, R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 131

Compounds of the formula Ia.1 in which R⁶ is2-ethyl-3-oxo-isoxazolidin-4-yl, R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 132

Compounds of the formula Ia.1 in which R⁶ is2-propyl-3-oxo-isoxazolidin-4-yl, R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 133

Compounds of the formula Ia.1 in which R⁶ is2-butyl-3-oxo-isoxazolidin-4-yl, R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 134

Compounds of the formula Ia.1 in which R⁶ is2-(but-2-yl)-3-oxo-isoxazolidin-4-yl, R⁵ is hydrogen, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 135

Compounds of the formula Ia.1 in which R⁶ is2-(2-fluoroethyl)-3-oxo-isoxazolidin-4-yl, R⁵ is hydrogen, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 136

Compounds of the formula Ia.1 in which R⁶ is2-(2,2-difluoroethyl)-3-oxo-isoxazolidin-4-yl, R⁵ is hydrogen, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 137

Compounds of the formula Ia.1 in which R⁶ is2-(2,2,2-trifluoroethyl)-3-oxo-isoxazolidin-4-yl, R⁵ is hydrogen, andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 138

Compounds of the formula Ia.1 in which R⁶ is2-(3,3,3-trifluoropropyl)-3-oxo-isoxazolidin-4-yl, R⁵ is hydrogen, andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 139

Compounds of the formula Ia.1 in which R⁶ is1-methyl-5-oxo-1,2,4-triazol-4-yl, R⁵ is hydrogen, and the combinationof R^(2a), R^(2b) and R^(2c) for a compound corresponds in each case toone row of Table A

Table 140

Compounds of the formula Ia.1 in which R⁶ is azetidin-3-yl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 141

Compounds of the formula Ia.1 in which R⁶ is 1-acetyl-azetidin-3-yl, R⁵is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 142

Compounds of the formula Ia.1 in which R⁶ is NH₂, R⁵ is hydrogen, andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 143

Compounds of the formula Ia.1 in which R⁶ is —NH-phenyl, R⁵ is hydrogen,and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 144

Compounds of the formula Ia.1 in which R⁶ is —NH-pyridin-2-yl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 145

Compounds of the formula Ia.1 in which R⁶ is —NH-pyridin-3-yl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 146

Compounds of the formula Ia.1 in which R⁶ is —NH-pyridin-4-yl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 147

Compounds of the formula Ia.1 in which R⁶ is —NH-pyrimidin-2-yl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 148

Compounds of the formula Ia.1 in which R⁶ is —NH-pyrimidin-4-yl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 149

Compounds of the formula Ia.1 in which R⁶ is —NH-pyrimidin-5-yl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 150

Compounds of the formula Ia.1 in which R⁶ is —N(CH₃)-pyrimidin-2-yl, R⁵is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 151

Compounds of the formula Ia.1 in which R⁶ is —CH₂—COOCH₃, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 152

Compounds of the formula Ia.1 in which R⁶ is —CH₂—COO—CH₂CH₃, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 153

Compounds of the formula Ia.1 in which R⁶ is —CH₂—CONH₂, R⁵ is hydrogen,and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 154

Compounds of the formula Ia.1 in which R⁶ is —CH₂—CONH—CH₃, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 155

Compounds of the formula Ia.1 in which R⁶ is —CH₂—CONH—CH₂CH₃, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 156

Compounds of the formula Ia.1 in which R⁶ is —CH₂—CONH—CH₂CH₂CH₃, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 157

Compounds of the formula Ia.1 in which R⁶ is —CH₂—CONH-isopropyl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 158

Compounds of the formula Ia.1 in which R⁶ is —CH₂—CONH—CH₂CH₂F, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 159

Compounds of the formula Ia.1 in which R⁶ is —CH₂—CONH—CH₂CH F₂, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 160

Compounds of the formula Ia.1 in which R⁶ is —CH₂—CONH—CH₂CF₃, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 161

Compounds of the formula Ia.1 in which R⁶ is —CH₂—CONH—CH(CF₃)CH₃, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 162

Compounds of the formula Ia.1 in which R⁶ is —CH₂—CONH—CH(CF₃)₂, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 163

Compounds of the formula Ia.1 in which R⁶ is —CH₂—CONH—CH₂CH₂CH F₂, R⁵is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 164

Compounds of the formula Ia.1 in which R⁶ is —CH₂—CONH—CH₂CH₂CF₃, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 165

Compounds of the formula Ia.1 in which R⁶ is —CH(CH₃)—CONH—CH₂CF₃, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 166

Compounds of the formula Ia.1 in which R⁶ is —CH₂—CONH-cyclopropyl, R⁵is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 167

Compounds of the formula Ia.1 in which R⁶ is —CH₂—CONH—CH₂CN, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 168

Compounds of the formula Ia.1 in which R⁶ is —CH₂—CONH—CH₂CH═CH₂, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 169

Compounds of the formula Ia.1 in which R⁶ is —CH₂—CONH—CH₂C≡CH, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 170

Compounds of the formula Ia.1 in which R⁶ is —CH₂—CONH—CH₂-cyclopropyl,R⁵ is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 171

Compounds of the formula Ia.1 in which R⁶ is—CH₂—CONH—CH₂-(1-cyano-cyclopropyl), R⁵ is hydrogen, and the combinationof R^(2a), R^(2b) and R^(2c) for a compound corresponds in each case toone row of Table A

Table 172

Compounds of the formula Ia.1 in which R⁶ is —CH₂—CONH-thietan-3-yl, R⁵is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 173

Compounds of the formula Ia.1 in which R⁶ is—CH₂—CONH-1-oxo-thietan-3-yl, R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 174

Compounds of the formula Ia.1 in which R⁶ is—CH₂—CONH-1,1-dioxo-thietan-3-yl, R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 175

Compounds of the formula Ia.1 in which R⁶ is benzyl, R⁵ is hydrogen, andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 176

Compounds of the formula Ia.1 in which R⁶ is pyridin-2-yl-methyl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 177

Compounds of the formula Ia.1 in which R⁶ is pyridin-3-yl-methyl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 178

Compounds of the formula Ia.1 in which R⁶ is pyridin-4-yl-methyl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 179

Compounds of the formula Ia.1 in which R⁶ is6-(trifluoromethyl)-pyridin-4-yl-methyl, R⁵ is hydrogen, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 180

Compounds of the formula Ia.1 in which R⁶ is pyrimidin-2-yl-methyl, R⁵is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 181

Compounds of the formula Ia.1 in which R⁶ is pyrimidin-4-yl-methyl, R⁵is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 182

Compounds of the formula Ia.1 in which R⁶ is pyrimidin-5-yl-methyl, R⁵is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 183

Compounds of the formula Ia.1 in which R⁶ is(4-fluoropyrimidin-2-yl)-methyl, R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 184

Compounds of the formula Ia.1 in which R⁶ is(5-fluoropyrimidin-2-yl)-methyl, R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 185

Compounds of the formula Ia.1 in which R⁶ is(4-chloropyrimidin-2-yl)-methyl, R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 186

Compounds of the formula Ia.1 in which R⁶ is(5-chloropyrimidin-2-yl)-methyl, R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 187

Compounds of the formula Ia.1 in which R⁶ is(4-bromopyrimidin-2-yl)-methyl, R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 188

Compounds of the formula Ia.1 in which R⁶ is(5-bromopyrimidin-2-yl)-methyl, R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 189

Compounds of the formula Ia.1 in which R⁶ is(4-methylpyrimidin-2-yl)-methyl, R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 190

Compounds of the formula Ia.1 in which R⁶ is(5-methylpyrimidin-2-yl)-methyl, R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 191

Compounds of the formula Ia.1 in which R⁶ is(4,6-dimethylpyrimidin-2-yl)-methyl, R⁵ is hydrogen, and the combinationof R^(2a), R^(2b) and R^(2c) for a compound corresponds in each case toone row of Table A

Table 192

Compounds of the formula Ia.1 in which R⁶ is(4-(trifluoromethyl)-pyrimidin-2-yl)-methyl, R⁵ is hydrogen, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 193

Compounds of the formula Ia.1 in which R⁶ is(5-(trifluoromethyl)-pyrimidin-2-yl)-methyl, R⁵ is hydrogen, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 194

Compounds of the formula Ia.1 in which R⁶ is(4,6-bis(trifluoromethyl)-pyrimidin-2-yl)-methyl, R⁵ is hydrogen, andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 195

Compounds of the formula Ia.1 in which R⁶ is(4-methyl-6-(trifluoromethyl)-pyrimidin-2-yl)-methyl, R⁵ is hydrogen,and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 196

Compounds of the formula Ia.1 in which R⁶ is pyridazin-3-yl-methyl, R⁵is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 197

Compounds of the formula Ia.1 in which R⁶ is pyridazin-4-yl-methyl, R⁵is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 198

Compounds of the formula Ia.1 in which R⁶ is pyrazin-2-yl-methyl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 199

Compounds of the formula Ia.1 in which R⁶ is pyrazol-3-yl-methyl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 200

Compounds of the formula Ia.1 in which R⁶ is1-methylpyrazol-3-yl-methyl, R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 201

Compounds of the formula Ia.1 in which R⁶ is2-methylpyrazol-3-yl-methyl, R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 202

Compounds of the formula Ia.1 in which R⁶ is thien-2-yl-methyl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 203

Compounds of the formula Ia.1 in which R⁶ is thien-3-yl-methyl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 204

Compounds of the formula Ia.1 in which R⁶ is thiazol-2-yl-methyl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 205

Compounds of the formula Ia.1 in which R⁶ is thiazol-4-yl-methyl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 206

Compounds of the formula Ia.1 in which R⁶ is thiazol-5-yl-methyl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 207

Compounds of the formula Ia.1 in which R⁶ is isothiazol-3-yl-methyl, R⁵is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 208

Compounds of the formula Ia.1 in which R⁶ is isothiazol-4-yl-methyl, R⁵is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 209

Compounds of the formula Ia.1 in which R⁶ is isothiazol-5-yl-methyl, R⁵is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 210

Compounds of the formula Ia.1 in which R⁶ is oxazol-2-yl-methyl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 211

Compounds of the formula Ia.1 in which R⁶ is oxazol-4-yl-methyl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 212

Compounds of the formula Ia.1 in which R⁶ is oxazol-5-yl-methyl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 213

Compounds of the formula Ia.1 in which R⁶ is isoxazol-3-yl-methyl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 214

Compounds of the formula Ia.1 in which R⁶ is isoxazol-4-yl-methyl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 215

Compounds of the formula Ia.1 in which R⁶ is isoxazol-5-yl-methyl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 216

Compounds of the formula Ia.1 in which R⁶ is1,2,3-1H-triazol-4-yl-methyl, R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 217

Compounds of the formula Ia.1 in which R⁶ is1-methyl-1,2,3-triazol-4-yl-methyl, R⁵ is hydrogen, and the combinationof R^(2a), R^(2b) and R^(2c) for a compound corresponds in each case toone row of Table A

Table 218

Compounds of the formula Ia.1 in which R⁶ is1,2,4-1H-triazol-3-yl-methyl, R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 219

Compounds of the formula Ia.1 in which R⁶ is1-methyl-1,2,4-triazol-3-yl-methyl, R⁵ is hydrogen, and the combinationof R^(2a), R^(2b) and R^(2c) for a compound corresponds in each case toone row of Table A

Table 220

Compounds of the formula Ia.1 in which R⁶ is4-methyl-1,2,4-triazol-3-yl-methyl, R⁵ is hydrogen, and the combinationof R^(2a), R^(2b) and R^(2c) for a compound corresponds in each case toone row of Table A

Table 221

Compounds of the formula Ia.1 in which R⁶ is1,2,4-oxadiazol-3-yl-methyl, R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 222

Compounds of the formula Ia.1 in which R⁶ is1,3,4-thiadiazol-2-yl-methyl, R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 223

Compounds of the formula Ia.1 in which R⁶ is1,2,3,4-1H-tetrazol-5-yl-methyl, R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 224

Compounds of the formula Ia.1 in which R⁶ is1-methyl-1,2,3,4-tetrazol-5-yl-methyl, R⁵ is hydrogen, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 225

Compounds of the formula Ia.1 in which R⁶ is1,2,3,4-2H-tetrazol-5-yl-methyl, R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 226

Compounds of the formula Ia.1 in which R⁶ is2-methyl-1,2,3,4-tetrazol-5-yl-methyl, R⁵ is hydrogen, and thecombination of R^(2a), R^(2b) and R^(2c) for a compound corresponds ineach case to one row of Table A

Table 227

Compounds of the formula Ia.1 in which R⁶ istetrahydrofuran-2-yl-methyl, R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 228

Compounds of the formula Ia.1 in which R⁶ istetrahydrofuran-3-yl-methyl, R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 229

Compounds of the formula Ia.1 in which R⁶ is 1,3-dioxolan-2-yl-methyl,R⁵ is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 230

Compounds of the formula Ia.1 in which R⁶ is2-(1,3-dioxolan-2-yl)-ethyl, R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 231

Compounds of the formula Ia.1 in which R⁶ is 2-pyridyl-eth-1-yl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 232

Compounds of the formula Ia.1 in which R⁶ is (1R)-2-pyridyl-eth-1-yl, R⁵is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 233

Compounds of the formula Ia.1 in which R⁶ is (1S)-2-pyridyl-eth-1-yl, R⁵is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 234

Compounds of the formula Ia.1 in which R⁶ is 1,3-dioxan-2-yl-methyl, R⁵is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 235

Compounds of the formula Ia.1 in which R⁶ is —CONH₂, R⁵ is hydrogen, andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 236

Compounds of the formula Ia.1 in which R⁶ is —CONH—CH₃, R⁵ is hydrogen,and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 237

Compounds of the formula Ia.1 in which R⁶ is —CONH—CH₂CH₃, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 238

Compounds of the formula Ia.1 in which R⁶ is —CONH-cyclopropyl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 239

Compounds of the formula Ia.1 in which R⁶ is —NHCO—NH—CH₃, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 240

Compounds of the formula Ia.1 in which R⁶ is —NHCO—NH—CH₂CH₃, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 241

Compounds of the formula Ia.1 in which R⁶ is —NHCO—NH—CH₂CH₂CH₃, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 242

Compounds of the formula Ia.1 in which R⁶ is —NHCO—NH—CH(CH₃)₂, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 243

Compounds of the formula Ia.1 in which R⁶ is —NHCO—NH—CH₂CF₃, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 244

Compounds of the formula Ia.1 in which R⁶ is —NHCO—NH—CH₂CHF₂, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 245

Compounds of the formula Ia.1 in which R⁶ is —NHCO—NH—CH(CH₃)CF₃, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 246

Compounds of the formula Ia.1 in which R⁶ is —NHCO—NH—CH(CF₃)₂, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 247

Compounds of the formula Ia.1 in which R⁶ is —NHCO—NH—CH₂CN, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 248

Compounds of the formula Ia.1 in which R⁶ is —NHCO—NH—CH₂—CH═CH₂, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 249

Compounds of the formula Ia.1 in which R⁶ is —NHCO—NH—CH₂—CH≡CH, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 250

Compounds of the formula Ia.1 in which R⁶ is —NHCO—NH-cyclopropyl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 251

Compounds of the formula Ia.1 in which R⁶ is—NHCO—NH-(1-cyanocyclopropyl), R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 252

Compounds of the formula Ia.1 in which R⁶ is —NHCO—NH-cyclobutyl, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 253

Compounds of the formula Ia.1 in which R⁶ is—NHCO—NH-(1-cyanocyclobutyl), R⁵ is hydrogen, and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Table 254

Compounds of the formula Ia.1 in which R⁶ is —NHCO—NH—CH₂-cyclopropyl,R⁵ is hydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 255

Compounds of the formula Ia.1 in which R⁶ is—NHCO—NH—CH₂-(1-cyanocyclopropyl), R⁵ is hydrogen, and the combinationof R^(2a), R^(2b) and R^(2c) for a compound corresponds in each case toone row of Table A

Table 256

Compounds of the formula Ia.1 in which R⁶ is —CH═NOCH₃, R⁵ is hydrogen,and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Table 257

Compounds of the formula Ia.1 in which R⁶ is —CH═NOCH₂CH₃, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 258

Compounds of the formula Ia.1 in which R⁶ is —CH═NOCH₂CF₃, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 259

Compounds of the formula Ia.1 in which R⁶ is —CH═NOCH₂CH═CH₂, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Table 260

Compounds of the formula Ia.1 in which R⁶ is —CH═NOCH₂C≡CH, R⁵ ishydrogen, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Tables 261 to 520

Compounds of the formula Ia.1 in which R⁶ is as defined in tables 1 to260, R⁵ is methyl, and the combination of R^(2a), R^(2b) and R^(2c) fora compound corresponds in each case to one row of Table A

Tables 521 to 780

Compounds of the formula Ia.1 in which R⁶ is as defined in tables 1 to260, R⁵ is ethyl, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Tables 781 to 1040

Compounds of the formula Ia.1 in which R⁶ is as defined in tables 1 to260, R⁵ is allyl, and the combination of R^(2a), R^(2b) and R^(2c) for acompound corresponds in each case to one row of Table A

Tables 1041 to 1300

Compounds of the formula Ia.1 in which R⁶ is as defined in tables 1 to260, R⁵ is propargyl, and the combination of R^(2a), R^(2b) and R^(2c)for a compound corresponds in each case to one row of Table A

Tables 1301 to 1560

Compounds of the formula Ia.1 in which R⁶ is as defined in tables 1 to260, R⁵ is —CH₂—CN, and the combination of R^(2a), R^(2b) and R^(2c) fora compound corresponds in each case to one row of Table A

Tables 1561 to 1820

Compounds of the formula Ia.1 in which R⁶ is as defined in tables 1 to260, R⁵ is —CH₂—OCH₃, and the combination of R^(2a), R^(2b) and R^(2c)for a compound corresponds in each case to one row of Table A

Table 1821

Compounds of the formula Ia.1 in which R⁵ and R⁶ formtogether=S(CH₂CH₃)₂ and the combination of R^(2a), R^(2b) and R^(2c) fora compound corresponds in each case to one row of Table A

Table 1822

Compounds of the formula Ia.1 in which R⁵, R⁶ and the nitrogen atom towhich they are bound form together 3-ethyl-4-oxo-imidazolidin-1-yl andthe combination of R^(2a), R^(2b) and R^(2c) for a compound correspondsin each case to one row of Table A

Table 1823

Compounds of the formula Ia.1 in which R⁵, R⁶ and the nitrogen atom towhich they are bound form together4-oxo-3-(2,2,2-trifluoroethyl)-imidazolidin-1-yl and the combination ofR^(2a), R^(2b) and R^(2c) for a compound corresponds in each case to onerow of Table A

Tables 1824 to 3646

Compounds of the formula Ia.2 in R⁵ and R⁶ are as defined in tables 1 to1823, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 3647 to 5469

Compounds of the formula Ia.3 in R⁵ and R⁶ are as defined in tables 1 to1823, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

Tables 5470 to 7292

Compounds of the formula Ia.4 in R⁵ and R⁶ are as defined in tables 1 to1823, and the combination of R^(2a), R^(2b) and R^(2c) for a compoundcorresponds in each case to one row of Table A

TABLE A No. R^(2a) R^(2b) R^(2c) A-1 F H F A-2 F F F A-3 F Cl F A-4 F BrF A-5 F H Cl A-6 F H Br A-7 Cl H Cl A-8 Cl Cl Cl A-9 Cl F Cl A-10 Cl BrCl A-11 Cl H Br A-12 Br H Br A-13 Br F Br A-14 Br Cl Br A-15 CF₃ H FA-16 CF₃ H Cl A-17 CF₃ H Br A-18 CF₃ H CF₃ A-19 CF₃ F F A-20 CF₃ Cl ClA-21 CF₃ Br Br A-22 OCF₃ H F A-23 OCF₃ H Cl A-24 OCF₃ H Br A-25 OCF₃ HCF₃ A-26 OCF₃ H H A-27 CF₃ H H A-28 Br H H A-29 Cl H H A-30 F H H A-31Cl F H

Among the above compounds, preference is given to compounds Ia.1 andIa.3.

In a specific embodiment, the compounds I are selected from thecompounds specified in the examples, either as a free base or in form ofan agriculturally or veterinarily acceptable salt, an N-oxide or astereoisomer thereof.

The compounds of the formula (I) can be prepared by the methods asdescribed in the below schemes or and in the synthesis descriptions ofthe working examples, or by standard methods of organic chemistry. Thesubstituents, variables and indices are as defined above for formula(I), if not otherwise specified.

Compounds of formula I wherein X¹ is O and wherein R^(3b) is hydrogen(termed below as compounds I.a) can be prepared by reacting a compoundof formula 1 as shown in scheme 1 below in an imination/Michael additionreaction with hydroxylamine. A′ is A or a precursor of A. Typicalprecursors of A are a halogen atom, CN, carboxy, C(O)OR^(z1) (carboxyand C(O)OR^(z1) are of course only “precursors” if in the desiredcompound I W is S and/or Rzl is not the desired radical R⁹ and/or if Yis to be —NR⁵R⁶) or —OSO₂—R^(z1), where R^(z1) is C₁-C₄-alkyl,C₁-C₄-haloalkyl or phenyl which may be substituted by 1, 2 or 3 radicalsselected from C₁-C₄-alkyl, C₁-C₄-haloalkyl C₁-C₄-alkoxy orC₁-C₄-haloalkoxy. Compounds I′ correspond to compounds I when A′ is A.Compounds I.a′ correspond to compounds I.a when A′ is A. Suitablereaction conditions are described, for example, in WO 2012/158396.Suitably, hydroxylamine is used as the hydrochloride salt. The reactionis generally carried out in the presence of a base, such as NaOH, KOH,Na₂CO₃ and the like. Suitable solvents are aqueous, such as water ormixtures of water with polar solvents, such as tetrahydrofuran, dioxaneand lower alkanols. If necessary (i.e. if A′ is a precursor of A), A′ isthen converted into a group A.

Compounds of formula I wherein X¹ is CH₂ and wherein R^(3b) is hydrogen(termed below as compounds I.b) can be prepared by first subjecting acompound of formula 1 to a Michael addition with nitromethane to 2, thenreducing the nitro group of 2 to an amino group. The resultingaminoketone reacts spontaneously to the pyrroline I.b′, as shown inscheme 2 below. Compounds I.b′ correspond to compounds I.b when A′ is A.Suitable reaction conditions are described, for example, in US2010/0298558. The Michael addition of nitromethane to 1 is carried outin the presence of a base. Suitable bases are for example alkalihydroxides and alcoholates, but preferably non-nucleophilic bases, suchas DBN or DBU, are used. Suitable solvents depend i.a. on the base used.If an alkali hydroxide is used, suitably an aqueous medium, such aswater of mixtures thereof with lower alkanols are used, while alkoxidesare used in the respective alcohol. If non-nucleophilic bases are used,polar, non-protic solvents, such as acetonitrile, tetrahydrofuran,dioxane and the like are preferred. If necessary (i.e. if A′ is aprecursor of A), A′ is then converted into a group A. Reduction of 2 iscarried out with a suitable reduction agent, such as Zn, Sn, Sn(II)salts, Fe or hydrogen-producing agents, such as ammonium formate in thepresence of Zn or Pd.

Compound 1 can be prepared in analogy to the method described inEP-A-2172462 and as shown in scheme 3 below by subjecting the ketones 3and 4 to an aldol condensation.

Ketone 3 can be obtained in analogy to the method described in US2011/0152246. Compounds I wherein W is O can be prepared by reacting acompound I′ wherein A′ is CI, Br, I or triflate with carbon monoxide inthe presence of a palladium catalyst and an alcohol ROH, wherein R isC₁-C₄-alkyl, to a compound of formula 5. Suitable palladium catalystsare for example those described in WO 2011/161130.

If desired, this ester is then hydrolyzed to the respective carboxylicacid, which is then reacted under standard amidation conditions with anamine NHR⁵R⁶. Hydrolyzation can be carried out under standardconditions, e.g. under acidic conditions using for example hydrochloricacid, sulfuric acid or trifluoroacetic acid, or under basic conditionsusing for example an alkali metal hydroxide, such as LiOH, NaOH or KOH.Amidation is preferably carried out by activation of the carboxylicacids with oxalylchloride [(COCl)₂] or thionylchloride (SOCl₂) to therespective acid chlorides, followed by reaction with an amine NHR⁵R⁶.Alternatively, amidation is carried out in the presence of a couplingreagent. Suitable coupling reagent (activators) are well known and arefor instance selected from carbodiimides, such as DCC(dicyclohexylcarbodiimide) and DCI (diisopropylcarbodiimide),benzotriazol derivatives, such as HATU(O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate), H BTU((O-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate)and HCTU (1H-benzotriazolium-1-[bis(dimethylamino)methylene]-5-chlorotetrafluoroborate) and phosphonium-derived activators, such as BOP((benzotriazol-1-yloxy)-tris(dimethyl-amino)phosphoniumhexafluorophosphate), Py-BOP((benzotriazol-1-yloxy)-tripyrrolidinphosphonium hexafluorophosphate)and Py-BrOP (bromotripyrroli-dinphosphonium hexafluorophosphate).Generally, the activator is used in excess. The benzotriazol andphosphonium coupling reagents are generally used in a basic medium.

Compounds I wherein W is S, can be prepared by reacting thecorresponding oxo-compound (W is O) with Lawesson's reagent (CAS19172-47-5), see for example Jesberger et al., Synthesis, 2003,1929-1958 and references therein. Solvents such as HMPA or THF at anelevated temperature such as 60° C. to 100° C. can be used. Preferredreaction conditions are THF at 65° C.

Compounds I wherein Y is OH can be prepared from compounds I wherein Yis hydrogen via oxidation of this aldehyde group A. Suitable conditionsare for example those of the Pinnick or Lindgren oxidation using achlorite, such as sodium chlorite NaClO₂ as oxidation agent. Asscavenger for the hypochlorite (HOCl) formed in the reaction,2-methyl-2-butene or hydrogen peroxide can be used. The Pinnick orLindgren oxidation is generally carried out in a water-containingsolvent under slightly acidic, buffered conditions (pH ca. 3-5; use of ahydrogen phosphate, e.g. NaH₂PO₄). Other suitable oxidation conditionsare described, for example, in WO 2011/022337. The resulting carboxylicacid can then be further esterified to give compounds I wherein Y is OR⁹wherein R⁹ is not hydrogen, or subjected to an amidation as describedabove to afford compounds I wherein Y is NR⁵R⁶.

Compounds I wherein R^(3b) is not hydrogen can be prepared fromcompounds I.a′ or I.b′ in analogy to the methods described in WO2010/020521 by reacting these with a base, such as lithiumdiisopropylamine, followed by the addition of an electrophile, e.g. ahalogenating agent, such as 4-iodotoluene difluoride,N-fluorobenzenesulfonimide (“NFSI”), N-chlorosuccinimide (“NCS”),N-bromosuccinimide (“NBS”) or N-iodosuccinimide (“NIS”), an alkylatingagent, such as an alkyl halide, e.g. methyl iodide, a sulfanylatingagent, such as methanesulfenyl chloride (CH₃S—Cl), S-methylmethanethiosulfonate (CH₃SO₂—SCH₃) or dimethyldisulfide (CH₃S—SCH₃), or,for introducing OH, a hydroxylating agent, such as oxaziridines (forinstance, N-sulfonyl oxaziridines) oroxodiperoxymolybdenum(pyridine)-(hexamethyl-phosphoric triamide)(“MoOPH”).

As a rule, the compounds of formula I including their stereoisomers,salts, and N-oxides, and their precursors in the synthesis process, canbe prepared by the methods described above. If individual compounds cannot be prepared via the above-described routes, they can be prepared byderivatization of other compounds I or the respective precursor or bycustomary modifications of the synthesis routes described. For example,in individual cases, certain compounds of formula (I) can advantageouslybe prepared from other compounds of formula (I) by derivatization, e.g.by ester hydrolysis, amidation, esterification, ether cleavage,olefination, reduction, oxidation and the like, or by customarymodifications of the synthesis routes described.

The reaction mixtures are worked up in the customary manner, for exampleby mixing with water, separating the phases, and, if appropriate,purifying the crude products by chromatography, for example on aluminaor on silica gel. Some of the intermediates and end products may beobtained in the form of colorless or pale brown viscous oils which arefreed or purified from volatile components under reduced pressure and atmoderately elevated temperature. If the intermediates and end productsare obtained as solids, they may be purified by recrystallization ortrituration.

Due to their excellent activity, the compounds of the present inventionmay be used for controlling invertebrate pests.

Accordingly, the present invention also provides a method forcontrolling invertebrate pests which method comprises treating thepests, their food supply, their habitat or their breeding ground or acultivated plant, plant propagation materials (such as seed), soil,area, material or environment in which the pests are growing or maygrow, or the materials, cultivated plants, plant propagation materials(such as seed), soils, surfaces or spaces to be protected from pestattack or infestation with a pesticidally effective amount of a compoundof the present invention or a composition as defined above. Theinvention also relates to the use of a compound of the invention, of astereoisomer and/or of an agriculturally or veterinarily acceptable saltthereof for combating invertebrate pests

Preferably, the method of the invention serves for protecting plantpropagation material (such as seed) and the plant which grows therefromfrom invertebrate pest attack or infestation and comprises treating theplant propagation material (such as seed) with a pesticidally effectiveamount of a compound of the present invention as defined above or with apesticidally effective amount of an agricultural composition as definedabove and below. The method of the invention is not limited to theprotection of the “substrate” (plant, plant propagation materials, soilmaterial etc.) which has been treated according to the invention, butalso has a preventive effect, thus, for example, according protection toa plant which grows from a treated plant propagation materials (such asseed), the plant itself not having been treated.

Alternatively preferably, the method of the invention serves forprotecting plants from attack or infestation by invertebrate pests,which method comprises treating the plants with a pesticidally effectiveamount of at least one compound of the invention, a stereoisomer thereofand/or at least one agriculturally acceptable salt thereof.

In the sense of the present invention, “invertebrate pests” arepreferably selected from arthropods and nematodes, more preferably fromharmful insects, arachnids and nematodes, and even more preferably frominsects, acarids and nematodes. In the sense of the present invention,“invertebrate pests” are most preferably insects.

The invention further provides an agricultural composition for combatinginvertebrate pests, which comprises such an amount of at least onecompound according to the invention and at least one inert liquid and/orsolid agronomically acceptable carrier that has a pesticidal action and,if desired, at least one surfactant. Such a composition may comprise asingle active compound of the present invention or a mixture of severalactive compounds of the present invention. The composition according tothe present invention may comprise an individual isomer or mixtures ofisomers or a salt as well as individual tautomers or mixtures oftautomers.

The compounds of the present invention, including their salts,stereoisomers and tautomers, are in particular suitable for efficientlycontrolling arthropodal pests such as arachnids, myriapedes and insectsas well as nematodes. They are especially suitable for efficientlycombating or controlling the following pests:

insects from the order of the lepidopterans (Lepidoptera), for exampleAcronicta major, Adoxophyes orana, Aedia leucomelas, Agrotis spp. suchas Agrotis fucosa, Agrotis segetum, Agrotis ipsilon; Alabama argillacea,Anticarsia gemmatalis, Anticarsia spp., Argyresthia conjugella,Autographa gamma, Barathra brassicae, Bucculatrix thurberiella, Bupaluspiniarius, Cacoecia murinana, Cacoecia podana, Capua reticulana,Carpocapsa pomonella, Cheimatobia brumata, Chilo spp. such as Chilosuppressalis; Choristoneura fumiferana, Choristoneura occidentalis,Cirphis unipuncta, Clysia ambiguella, Cnaphalocerus spp., Cydiapomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella,Earias insulana, Elasmopalpus lignosellus, Ephestia cautella, Ephestiakuehniella, Eupoecilia ambiguella, Euproctis chrysorrhoea, Euxoa spp.,Evetria bouliana, Feltia spp. such as Feltia subterranean; Galleriamellonella, Grapholitha funebrana, Grapholitha molesta, Helicoverpa spp.such as Helicoverpa armigera, Helicoverpa zea; Heliothis spp. such asHeliothis armigera, Heliothis virescens, Heliothis zea; Hellula undalis,Hibernia defoliaria, Hofmannophila pseudospretella, Homona magnanima,Hyphantria cunea, Hyponomeuta padella, Hyponomeuta malinellus, Keiferialycopersicella, Lambdina fiscellaria, Laphygma spp. such as Laphygmaexigua; Leucoptera coffeella, Leucoptera scitella, Lithocolletisblancardella, Lithophane antennata, Lobesia botrana, Loxagrotisalbicosta, Loxostege sticticalis, Lymantria spp. such as Lymantriadispar, Lymantria monacha; Lyonetia clerkella, Malacosoma neustria,Mamestra spp. such as Mamestra brassicae; Mocis repanda, Mythimnaseparata, Orgyia pseudotsugata, Oria spp., Ostrinia spp. such asOstrinia nubilalis; Oulema oryzae, Panolis flammea, Pectinophora spp.such as Pectinophora gossypiella; Peridroma saucia, Phalera bucephala,Phthorimaea spp. such as Phthorimaea operculella; Phyllocnistiscitrella, Pieris spp. such as Pieris brassicae, Pieris rapae; Plathypenascabra, Plutella maculipennis, Plutella xylostella, Prodenia spp.,Pseudaletia spp., Pseudoplusia includens, Pyrausta nubilalis, Rhyacioniafrustrana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothispilleriana, Spodoptera spp. such as Spodoptera frugiperda, Spodopteralittoralis, Spodoptera litura; Thaumatopoea pityocampa, Thermesiagemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana,Trichoplusia spp. such as Trichoplusia ni; Tuta absoluta, and Zeirapheracanadensis,

beetles (Coleoptera), for example Acanthoscehdes obtectus, Adoretusspp., Agelastica alni, Agrilus sinuatus, Agriotes spp. such as Agriotesfuscicollis, Agriotes lineatus, Agriotes obscurus; Amphimallussolstitialis, Anisandrus dispar, Anobium punctatum, Anomala rufocuprea,Anoplophora spp. such as Anoplophora glabripennis; Anthonomus spp. suchas Anthonomus grandis, Anthonomus pomorum; Anthrenus spp., Aphthonaeuphoridae, Apogonia spp., Athous haemorrhoidalis, Atomaria spp. such asAtomaria linearis; Attagenus spp., Aulacophora femoralis, Blastophaguspiniperda, Blitophaga undata, Bruchidius obtectus, Bruchus spp. such asBruchus lentis, Bruchus pisorum, Bruchus rufimanus; Byctiscus betulae,Callosobruchus chinensis, Cassida nebulosa, Cerotoma trifurcata, Cetoniaaurata, Ceuthorhynchus spp. such as Ceuthorrhynchus assimilis,Ceuthorrhynchus napi; Chaetocnema tibialis, Cleonus mendicus, Conoderusspp. such as Conoderus vespertinus; Cosmopolites spp., Costelytrazealandica, Crioceris asparagi, Cryptorhynchus lapathi, Ctenicera ssp.such as Ctenicera destructor; Curculio spp., Dectes texanus, Dermestesspp., Diabrotica spp. such as Diabrotica 12-punctata Diabroticaspeciosa, Diabrotica longicornis, Diabrotica semipunctata, Diabroticavirgifera; Epilachna spp. such as Epilachna varivestis, Epilachnavigintioctomaculata; Epitrix spp. such as Epitrix hirtipennis;Eutinobothrus brasiliensis, Faustinus cubae, Gibbium psylloides,Heteronychus arator, Hylamorpha elegans, Hylobius abietis, Hylotrupesbajulus, Hypera brunneipennis, Hypera postica, Hypothenemus spp., Ipstypographus, Lachnosterna consanguinea, Lema bilineata, Lema melanopus,Leptinotarsa spp. such as Leptinotarsa decemlineata; Limoniuscalifornicus, Lissorhoptrus oryzophilus, Lissorhoptrus oryzophilus,Lixus spp., Lyctus spp. such as Lyctus bruneus; Melanotus communis,Meligethes spp. such as Meligethes aeneus; Melolontha hippocastani,Melolontha melolontha, Migdolus spp., Monochamus spp. such as Monochamusalternatus; Naupactus xanthographus, Niptus hololeucus, Oryctesrhinoceros, Oryzaephilus surinamensis, Otiorrhynchus sulcatus,Otiorrhynchus ovatus, Otiorrhynchus sulcatus, Oulema oryzae, Oxycetoniajucunda, Phaedon cochleariae, Phyllobius pyri, Phyllopertha horticola,Phyllophaga spp., Phyllotreta spp. such as Phyllotreta chrysocephala,Phyllotreta nemorum, Phyllotreta striolata; Phyllophaga spp.,Phyllopertha horticola, Popillia japonica, Premnotrypes spp., Psylliodeschrysocephala, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica,Sitona lineatus, Sitophilus spp. such as Sitophilus granaria, Sitophiluszeamais; Sphenophorus spp. such as Sphenophorus levis; Sternechus spp.such as Sternechus subsignatus; Symphyletes spp., Tenebrio molitor,Tribolium spp. such as Tribolium castaneum; Trogoderma spp., Tychiusspp., Xylotrechus spp., and Zabrus spp. such as Zabrus tenebrioides,

flies, mosquitoes (Diptera), e.g. Aedes spp. such as Aedes aegypti,Aedes albopictus, Aedes vexans; Anastrepha ludens, Anopheles spp. suchas Anopheles albimanus, Anopheles crucians, Anopheles freeborni,Anopheles gambiae, Anopheles leucosphyrus, Anopheles maculipennis,Anopheles minimus, Anopheles quadrimaculatus, Anopheles sinensis; Bibiohortulanus, Calliphora erythrocephala, Calliphora vicina, Cerafitiscapitata, Ceratitis capitata, Chrysomyia spp. such as Chrysomyabezziana, Chrysomya hominivorax, Chrysomya macellaria; Chrysopsatlanticus, Chrysops discalis, Chrysops silacea, Cochliomyia spp. suchas Cochliomyia hominivorax; Contarinia spp. such as Contariniasorghicola; Cordylobia anthropophaga, Culex spp. such as Culexnigripalpus, Culex pipiens, Culex quinquefasciatus, Culex tarsalis,Culex tritaeniorhynchus; Culicoides furens, Culiseta inornata, Culisetamelanura, Cuterebra spp., Dacus cucurbitae, Dacus oleae, Dasineurabrassicae, Delia spp. such as Delia antique, Delia coarctata, Deliaplatura, Delia radicum; Dermatobia hominis, Drosophila spp., Fannia spp.such as Fannia canicularis; Gastraphilus spp. such as Gasterophilusintestinalis; Geomyza Tripunctata, Glossina fuscipes, Glossinamorsitans, Glossina palpalis, Glossina tachinoides, Haematobia irritans,Haplodiplosis equestris, Hippelates spp., Hylemyia spp. such as Hylemyiaplatura; Hypoderma spp. such as Hypoderma lineata; Hyppobosca spp.,Leptoconops torrens, Liriomyza spp. such as Liriomyza sativae, Liriomyzatrifolii; Lucilia spp. such as Lucilia caprina, Lucilia cuprina, Luciliasericata; Lycoria pectoralis, Mansonia titillanus, Mayetiola spp. suchas Mayetiola destructor; Musca spp. such as Musca autumnalis, Muscadomestica; Muscina stabulans, Oestrus spp. such as Oestrus ovis; Opomyzaflorum, Oscinella spp. such as Oscinella frit; Pegomya hysocyami,Phlebotomus argentipes, Phorbia spp. such as Phorbia antiqua, Phorbiabrassicae, Phorbia coarctata; Prosimulium mixtum, Psila rosae,Psorophora columbiae, Psorophora discolor, Rhagoletis cerasi, Rhagoletispomonella, Sarcophaga spp. such as Sarcophaga haemorrhoidalis; Simuliumvittatum, Stomoxys spp. such as Stomoxys calcitrans; Tabanus spp. suchas Tabanus atratus, Tabanus bovinus, Tabanus lineola, Tabanus similis;Tannia spp., Tipula oleracea, Tipula paludosa, and Wohlfahrtia spp.,

thrips (Thysanoptera), e.g. Baliothrips biformis, Dichromothripscorbetti, Dichromothrips ssp., Enneothrips flavens, Frankliniella spp.such as Frankliniella fusca, Frankliniella occidentalis, Frankliniellatritici; Heliothrips spp., Hercinothrips femoralis, Kakothrips spp.,Rhipiphorothrips cruentatus, Scirtothrips spp. such as Scirtothripscitri; Taeniothrips cardamoni, Thrips spp. such as Thrips oryzae, Thripspalmi, Thrips tabaci;

termites (Isoptera), e.g. Calotermes flavicollis, Coptotermesformosanus, Heterotermes aureus, Heterotermes longiceps, Heterotermestenuis, Leucotermes flavipes, Odontotermes spp., Reticulitermes spp.such as Reticulitermes speratus, Reticulitermes flavipes, Reticulitermesgrassei, Reticulitermes lucifugus, Reticulitermes santonensis,Reticulitermes virginicus; Termes natalensis,

cockroaches (Blattaria-Blattodea), e.g. Acheta domesticus, Blattaorientalis, Blattella asahinae, Blattella germanica, Gryllotalpa spp.,Leucophaea maderae, Locusta spp., Melanoplus spp., Periplanetaamericana, Periplaneta australasiae, Periplaneta brunnea, Periplanetafuligginosa, Periplaneta japonica,

bugs, aphids, leafhoppers, whiteflies, scale insects, cicadas(Hemiptera), e.g. Acrosternum spp. such as Acrosternum hilare;Acyrthosipon spp. such as Acyrthosiphon onobrychis, Acyrthosiphon pisum;Adelges laricis, Aeneolamia spp., Agonoscena spp., Aleurodes spp.,Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anasa tristis,Antestiopsis spp., Anuraphis cardui, Aonidiella spp., Aphanostigma piri,Aphidula nasturtii, Aphis spp. such as Aphis fabae, Aphis forbesi, Aphisgossypii, Aphis grossulariae, Aphis pomi, Aphis sambuci, Aphisschneideri, Aphis spiraecola; Arboridia apicalis, Arilus critatus,Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthum solani,Bemisia spp. such as Bemisia argentifolii, Bemisia tabaci; Blissus spp.such as Blissus leucopterus; Brachycaudus cardui, Brachycaudushelichrysi, Brachycaudus persicae, Brachycaudus prunicola, Brachycolusspp., Brevicoryne brassicae, Calligypona marginata, Calocoris spp.,Campylomma livida, Capitophorus horni, Carneocephala fulgida, Caveleriusspp., Ceraplastes spp., Ceratovacuna lanigera, Cercopidae, Cerosiphagossypii, Chaetosiphon fragaefolii, Chionaspis tegalensis, Chloritaonukii, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila,Cimex spp. such as Cimex hemipterus, Cimex lectularius; Coccomytilushalli, Coccus spp., Creontiades dilutus, Cryptomyzus ribis, Cryptomyzusribis, Cyrtopeltis notatus, Dalbulus spp., Dasynus piperis, Dialeuradesspp., Diaphorina spp., Diaspis spp., Dichelops furcatus, Diconocorishewetti, Doralis spp., Dreyfusia nordmannianae, Dreyfusia piceae,Drosicha spp., Dysaphis spp. such as Dysaphis plantaginea, Dysaphispyri, Dysaphis radicola; Dysaulacorthum pseudosolani, Dysdercus spp.such as Dysdercus cingulatus, Dysdercus intermedius; Dysmicoccus spp.,Empoasca spp. such as Empoasca fabae, Empoasca solana; Eriosoma spp.,Erythroneura spp., Eurygaster spp. such as Eurygaster integriceps;Euscelis bilobatus, Euschistus spp. such as Euschistuos heros,Euschistus impictiventris, Euschistus servus; Geococcus coffeae,Halyomorpha spp. such as Halyomorpha halys; Heliopeltis spp.,Homalodisca coagulata, Horcias nobilellus, Hyalopterus pruni,Hyperomyzus lactucae, Icerya spp., Idiocerus spp., Idioscopus spp.,Laodelphax striatellus, Lecanium spp., Lepidosaphes spp., Leptocorisaspp., Leptoglossus phyllopus, Lipaphis erysimi, Lygus spp. such as Lygushesperus, Lygus lineolaris, Lygus pratensis; Macropes excavatus,Macrosiphum spp. such as Macrosiphum rosae, Macrosiphum avenae,Macrosiphum euphorbiae; Mahanarva fimbriolata, Megacopta cribraria,Megoura viciae, Melanaphis pyrarius, Melanaphis sacchari, Metcafiellaspp., Metopolophium dirhodum, Miridae spp., Monellia costalis,Monelliopsis pecanis, Myzus spp. such as Myzus ascalonicus, Myzuscerasi, Myzus persicae, Myzus varians; Nasonovia ribis-nigri,Nephotettix spp. such as Nephotettix malayanus, Nephotettix nigropictus,Nephotettix parvus, Nephotettix virescens; Nezara spp. such as Nezaraviridula; Nilaparvata lugens, Oebalus spp., Oncometopia spp., Ortheziapraelonga, Parabemisia myricae, Paratrioza spp., Parlatoria spp.,Pemphigus spp. such as Pemphigus bursarius; Pentomidae, Peregrinusmaidis, Perkinsiella saccharicida, Phenacoccus spp., Phloeomyzuspasserinii, Phorodon humuli, Phylloxera spp., Piesma quadrata,Piezodorus spp. such as Piezodorus guildinii, Pinnaspis aspidistrae,Planococcus spp., Protopulvinaria pyriformis, Psallus seriatus,Pseudacysta persea, Pseudaulacaspis pentagona, Pseudococcus spp. such asPseudococcus comstocki; Psylla spp. such as Psylla mali, Psylla piri;Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., Quesada gigas,Rastrococcus spp., Reduvius senilis, Rhodnius spp., Rhopalomyzusascalonicus, Rhopalosiphum spp. such as Rhopalosiphum pseudobrassicas,Rhopalosiphum insertum, Rhopalosiphum maidis, Rhopalosiphum padi;Sagatodes spp., Sahlbergella singularis, Saissetia spp., Sappaphis mala,Sappaphis mali, Scaphoides titanus, Schizaphis graminum, Schizoneuralanuginosa, Scotinophora spp., Selenaspidus articulatus, Sitobionavenae, Sogata spp., Sogatella furcifera, Solubea insularis, Stephanitisnashi, Stictocephala festina, Tenalaphara malayensis, Thyanta spp. suchas Thyanta perditor; Tibraca spp., Tinocallis caryaefoliae, Tomaspisspp., Toxoptera spp. such as Toxoptera aurantii; Trialeurodes spp. suchas Trialeurodes vaporariorum; Triatoma spp., Trioza spp., Typhlocybaspp., Unaspis spp. such as Unaspis yanonensis; and Viteus vitifolii,

ants, bees, wasps, sawflies (Hymenoptera), e.g. Athalia rosae, Attacapiguara, Atta cephalotes, Atta cephalotes, Atta laevigata, Attarobusta, Atta sexdens, Atta texana, Bombus spp., Camponotus floridanus,Crematogaster spp., Dasymutilla occidentalis, Diprion spp.,Dolichovespula maculata, Hoplocampa spp. such as Hoplocampa minuta,Hoplocampa testudinea; Lasius spp. such as Lasius niger, Linepithemahumile, Monomorium pharaonis, Paravespula germanica, Paravespulapennsylvanica, Paravespula vulgaris, Pheidole megacephala, Pogonomyrmexbarbatus, Pogonomyrmex californicus, Polistes rubiginosa, Solenopsisgeminata, Solenopsis invicta, Solenopsis richteri, Solenopsis xyloni,Vespa spp. such as Vespa crabro, and Vespula squamosa,

crickets, grasshoppers, locusts (Orthoptera), e.g. Acheta domestica,Calliptamus italicus, Chortoicetes terminifera, Dociostaurus maroccanus,Gryllotalpa africana, Gryllotalpa gryllotalpa, Hieroglyphus daganensis,Kraussaria angulifera, Locusta migratoria, Locustana pardalina,Melanoplus bivittatus, Melanoplus femurrubrum, Melanoplus mexicanus,Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata,Oedaleus senegalensis, Schistocerca americana, Schistocerca gregaria,Tachycines asynamorus, and Zonozerus variegatus,

arachnids (Arachnida), such as acari, e.g. of the families Argasidae,Ixodidae and Sarcoptidae, such as Amblyomma spp. (e.g. Amblyommaamericanum, Amblyomma variegatum, Amblyomma maculatum), Argas spp. (e.g.Argas persicus), Boophilus spp. (e.g. Boophilus annulatus, Boophilusdecoloratus, Boophilus microplus), Dermacentor silvarum, Dermacentorandersoni, Dermacentor variabilis, Hyalomma spp. (e.g. Hyalommatruncatum), Ixodes spp. (e.g. Ixodes ricinus, Ixodes rubicundus, Ixodesscapularis, Ixodes holocyclus, Ixodes pacificus), Ornithodorus spp.(e.g. Ornithodorus moubata, Ornithodorus hermsi, Ornithodorus turicata),Ornithonyssus bacoti, Otobius megnini, Dermanyssus gallinae, Psoroptesspp. (e.g. Psoroptes ovis), Rhipicephalus spp. (e.g. Rhipicephalussanguineus, Rhipicephalus appendiculatus, Rhipicephalus evertsi),Rhizoglyphus spp., Sarcoptes spp. (e.g. Sarcoptes scabiei), andEriophyidae spp. such as Acaria sheldoni, Aculops spp. (e.g. Aculopspelekassi) Aculus spp. (e.g. Aculus schlechtendali), Epitrimerus pyri,Phyllocoptruta oleivora and Eriophyes spp. (e.g. Eriophyes sheldoni);Tarsonemidae spp. such as Hemitarsonemus spp., Phytonemus pallidus andPolyphagotarsonemus latus, Stenotarsonemus spp.; Tenuipalpidae spp. suchas Brevipalpus spp. (e.g. Brevipalpus phoenicis); Tetranychidae spp.such as Eotetranychus spp., Eutetranychus spp., Oligonychus spp.,Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus,Tetranychus telarius and Tetranychus urticae; Bryobia praetiosa,Panonychus spp. (e.g. Panonychus ulmi, Panonychus citri),Metatetranychus spp. and Oligonychus spp. (e.g. Oligonychus pratensis),Vasates lycopersici; Araneida, e.g. Latrodectus mactans, and Loxoscelesreclusa. And Acarus siro, Chorioptes spp., Scorpio maurus

fleas (Siphonaptera), e.g. Ceratophyllus spp., Ctenocephalides felis,Ctenocephalides canis, Xenopsylla cheopis, Pulex irritans, Tungapenetrans, and Nosopsyllus fasciatus,

silverfish, firebrat (Thysanura), e.g. Lepisma saccharina and Thermobiadomestica,

centipedes (Chilopoda), e.g. Geophilus spp., Scutigera spp. such asScutigera coleoptrata;

millipedes (Diplopoda), e.g. Blaniulus guttulatus, Narceus spp.,

Earwigs (Dermaptera), e.g. forficula auricularia,

lice (Phthiraptera), e.g. Damalinia spp., Pediculus spp. such asPediculus humanus capitis, Pediculus humanus corporis; Pthirus pubis,Haematopinus spp. such as Haematopinus eurysternus, Haematopinus suis;Linognathus spp. such as Linognathus vituli; Bovicola bovis, Menopongallinae, Menacanthus stramineus and Solenopotes capillatus,Trichodectes spp.,

springtails (Collembola), e.g. Onychiurus ssp. such as Onychiurusarmatus,

They are also suitable for controlling nematodes: plant parasiticnematodes such as root knot nematodes, Meloidogyne hapla, Meloidogyneincognita, Meloidogyne javanica, and other Meloidogyne species;cyst-forming nematodes, Globodera rostochiensis and other Globoderaspecies; Heterodera avenae, Heterodera glycines, Heterodera schachtii,Heterodera trifolii, and other Heterodera species; Seed gall nematodes,Anguina species; Stem and foliar nematodes, Aphelenchoides species suchas Aphelenchoides besseyi; Sting nematodes, Belonolaimus longicaudatusand other Belonolaimus species; Pine nematodes, Bursaphelenchuslignicolus Mamiya et Kiyohara, Bursaphelenchus xylophilus and otherBursaphelenchus species; Ring nematodes, Criconema species, Criconemellaspecies, Criconemoides species, Mesocriconema species; Stem and bulbnematodes, Ditylenchus destructor, Ditylenchus dipsaci and otherDitylenchus species; Awl nematodes, Dolichodorus species; Spiralnematodes, Heliocotylenchus multicinctus and other Helicotylenchusspecies; Sheath and sheathoid nematodes, Hemicycliophora species andHemicriconemoides species; Hirshmanniella species; Lance nematodes,Hoploaimus species; false rootknot nematodes, Nacobbus species; Needlenematodes, Longidorus elongatus and other Longidorus species; Lesionnematodes, Pratylenchus brachyurus, Pratylenchus neglectus, Pratylenchuspenetrans, Pratylenchus curvitatus, Pratylenchus goodeyi and otherPratylenchus species; Burrowing nematodes, Radopholus similis and otherRadopholus species; Reniform nematodes, Rotylenchus robustus,Rotylenchus reniformis and other Rotylenchus species; Scutellonemaspecies; Stubby root nematodes, Trichodorus primitivus and otherTrichodorus species, Paratrichodorus species; Stunt nematodes,Tylenchorhynchus claytoni, Tylenchorhynchus dubius and otherTylenchorhynchus species; Citrus nematodes, Tylenchulus species such asTylenchulus semipenetrans; Dagger nematodes, Xiphinema species; andother plant parasitic nematode species.

Examples of further pest species which may be controlled by compounds offormula (I) include: from the class of the Bivalva, for example,Dreissena spp.; from the class of the Gastropoda, for example, Arionspp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp.,Lymnaea spp., Oncomelania spp., Succinea spp.; from the class of thehelminths, for example, Ancylostoma duodenale, Ancylostoma ceylanicum,Acylostoma braziliensis, Ancylostoma spp., Ascaris lumbricoides, Ascarisspp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp.,Clonorchis spp., Cooperia spp., Dicrocoelium spp., Dictyocaulus filaria,Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus,Echinococcus multilocularis, Enterobius vermicularis, Faciola spp.,Haemonchus spp. such as Haemonchus contortus; Heterakis spp.,Hymenolepis nana, Hyostrongulus spp., Loa Loa, Nematodirus spp.,Oesophagostomum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagiaspp., Paragonimus spp., Schistosomen spp., Strongyloides fuelleborni,Strongyloides stercora lis, Stronyloides spp., Taenia saginata, Taeniasolium, Trichinella spiralis, Trichinella nativa, Trichinella britovi,Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp.,Trichuris trichiura, Wuchereria bancrofti; from the order of theIsopoda, for example, Armadillidium vulgare, Oniscus asellus, Porcellioscaber; from the order of the Symphyla, for example, Scutigerellaimmaculata;

Further examples of pest species which may be controlled by compounds offormula (I) include: Anisoplia austriaca, Apamea spp., Austroascaviridigrisea, Baliothrips biformis, Caenorhabditis elegans, Cephus spp.,Ceutorhynchus napi, Chaetocnema aridula, Chilo auricilius, Chiloindicus, Chilo polychrysus, Chortiocetes terminifera, Cnaphalocrocimedinalis, Cnaphalocrosis spp., Colias eurytheme, Collops spp.,Cornitermes cumulans, Creontiades spp., Cyclocephala spp., Dalbulusmaidis, Deraceras reticulatum, Diatrea saccharalis, Dichelops furcatus,Dicladispa armigera, Diloboderus spp. such as Diloboderus abderus;Edessa spp., Epinotia spp., Formicidae, Geocoris spp., Globitermessulfureus, Gryllotalpidae, Halotydeus destructor, Hipnodes bicolor,Hydrellia philippina, Julus spp., Laodelphax spp., Leptocorsia acuta,Leptocorsia oratorius, Liogenys fuscus, Lucillia spp., Lyogenys fuscus,Mahanarva spp., Maladera matrida, Marasmia spp., Mastotermes spp.,Mealybugs, Megascelis ssp, Metamasius hemipterus, Microtheca spp., Mocislatipes, Murgantia spp., Mythemina separata, Neocapritermes opacus,Neocapritermes parvus, Neomegalotomus spp., Neotermes spp., Nymphuladepunctalis, Oebalus pugnax, Orseolia spp. such as Orseolia oryzae;Oxycaraenus hyalinipennis, Plusia spp., Pomacea canaliculata,Procornitermes ssp, Procornitermes triacifer, Psylloides spp.,Rachiplusia spp., Rhodopholus spp., Scaptocoris castanea, Scaptocorisspp., Scirpophaga spp. such as Scirpophaga incertulas, Scirpophagainnotata; Scotinophara spp. such as Scotinophara coarctata; Sesamia spp.such as Sesamia inferens, Sogaella frucifera, Solenapsis geminata,Spissistilus spp., Stalk borer, Stenchaetothrips biformis,Steneotarsonemus spinki, Sylepta derogata, Telehin licus,Trichostrongylus spp.

The compounds of the present invention, including their salts,stereoisomers and tautomers, are particularly useful for controllinginsects, preferably sucking or piercing and chewing and biting insectssuch as insects from the genera Lepidoptera, Coleoptera and Hemiptera,in particular Lepidoptera, Coleoptera and true bugs. The compounds ofthe present invention, including their salts, stereoisomers andtautomers, are moreover useful for controlling insects of the ordersThysanoptera, Diptera (especially flies, mosquitos), Hymenoptera(especially ants) and Isoptera (especially termites.

The compounds of the present invention, including their salts,stereoisomers and tautomers, are particularly useful for controllinginsects of the orders Lepidoptera and Coleoptera.

The invention also relates to agrochemical compositions comprising anauxiliary and at least one compound I according to the invention.

An agrochemical composition comprises a pesticidally effective amount ofa compound I. The term “effective amount” denotes an amount of thecomposition or of the compounds I, which is sufficient for controllingharmful fungi on cultivated plants or in the protection of materials andwhich does not result in a substantial damage to the treated plants.Such an amount can vary in a broad range and is dependent on variousfactors, such as the species to be controlled, the treated cultivatedplant or material, the climatic conditions and the specific compound Iused.

The compounds I, their N-oxides and salts can be converted intocustomary types of agrochemical compositions, e.g. solutions, emulsions,suspensions, dusts, powders, pastes, granules, pressings, capsules, andmixtures thereof. Examples for composition types are suspensions (e.g.SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW,EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powdersor dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT),granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN),as well as gel formulations for the treatment of plant propagationmaterials such as seeds (e.g. GF). These and further compositions typesare defined in the “Catalogue of pesticide formulation types andinternational coding system”, Technical Monograph No. 2, 6^(th) Ed. May2008, CropLife International.

The compositions are prepared in a known manner, such as described byMollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001;or Knowles, New developments in crop protection product formulation,Agrow Reports DS243, T&F Informa, London, 2005.

Suitable auxiliaries are solvents, liquid carriers, solid carriers orfillers, surfactants, dispersants, emulsifiers, wetters, adjuvants,solubilizers, penetration enhancers, protective colloids, adhesionagents, thickeners, humectants, repellents, attractants, feedingstimulants, compatibilizers, bactericides, anti-freezing agents,anti-foaming agents, colorants, tackifiers and binders.

Suitable solvents and liquid carriers are water and organic solvents,such as mineral oil fractions of medium to high boiling point, e.g.kerosene, diesel oil; oils of vegetable or animal origin; aliphatic,cyclic and aromatic hydrocarbons, e.g. toluene, paraffin,tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol,propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones,e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acidesters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides,e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixturesthereof.

Suitable solid carriers or fillers are mineral earths, e.g. silicates,silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite,diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate,magnesium oxide; polysaccharides, e.g. cellulose, starch; fertilizers,e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas;products of vegetable origin, e.g. cereal meal, tree bark meal, woodmeal, nutshell meal, and mixtures thereof.

Suitable surfactants are surface-active compounds, such as anionic,cationic, nonionic and amphoteric surfactants, block polymers,polyelectrolytes, and mixtures thereof. Such surfactants can be used asemusifier, dispersant, solubilizer, wetter, penetration enhancer,protective colloid, or adjuvant. Examples of surfactants are listed inMcCutcheon's, Vol. 1: Emulsifiers & Detergents, McCutcheon'sDirectories, Glen Rock, USA, 2008 (International Ed. or North AmericanEd.).

Suitable anionic surfactants are alkali, alkaline earth or ammoniumsalts of sulfonates, sulfates, phosphates, carboxylates, and mixturesthereof. Examples of sulfonates are alkylarylsulfonates,diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates,sulfonates of fatty acids and oils, sulfonates of ethoxylatedalkylphenols, sulfonates of alkoxylated arylphenols, sulfonates ofcondensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes,sulfonates of naphthalenes and alkyl-naphthalenes, sulfosuccinates orsulfosuccinamates. Examples of sulfates are sulfates of fatty acids andoils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols,or of fatty acid esters. Examples of phosphates are phosphate esters.Examples of carboxylates are alkyl carboxylates, and carboxylatedalcohol or alkylphenol ethoxylates.

Suitable nonionic surfactants are alkoxylates, N-substituted fatty acidamides, amine oxides, esters, sugar-based surfactants, polymericsurfactants, and mixtures thereof. Examples of alkoxylates are compoundssuch as alcohols, alkylphenols, amines, amides, arylphenols, fatty acidsor fatty acid esters which have been alkoxylated with 1 to 50equivalents. Ethylene oxide and/or propylene oxide may be employed forthe alkoxylation, preferably ethylene oxide. Examples of N-substitutedfatty acid amides are fatty acid glucamides or fatty acid alkanolamides.Examples of esters are fatty acid esters, glycerol esters ormonoglycerides. Examples of sugar-based surfactants are sorbitans,ethoxylated sorbitans, sucrose and glucose esters oralkylpolyglucosides. Examples of polymeric surfactants are home- orcopolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.

Suitable cationic surfactants are quaternary surfactants, for examplequaternary ammonium compounds with one or two hydrophobic groups, orsalts of long-chain primary amines. Suitable amphoteric surfactants arealkylbetains and imidazolines. Suitable block polymers are blockpolymers of the A-B or A-B-A type comprising blocks of polyethyleneoxide and polypropylene oxide, or of the A-B—C type comprising alkanol,polyethylene oxide and polypropylene oxide. Suitable polyelectrolytesare polyacids or polybases. Examples of polyacids are alkali salts ofpolyacrylic acid or polyacid comb polymers. Examples of polybases arepolyvinylamines or polyethyleneamines.

Suitable adjuvants are compounds, which have a neglectable or even nopesticidal activity themselves, and which improve the biologicalperformance of the compound I on the target. Examples are surfactants,mineral or vegetable oils, and other auxilaries. Further examples arelisted by Knowles, Adjuvants and additives, Agrow Reports DS256, T&FInforma UK, 2006, chapter 5.

Suitable thickeners are polysaccharides (e.g. xanthan gum,carboxymethylcellulose), anorganic clays (organically modified orunmodified), polycarboxylates, and silicates.

Suitable bactericides are bronopol and isothiazolinone derivatives suchas alkylisothiazolinones and benzisothiazolinones.

Suitable anti-freezing agents are ethylene glycol, propylene glycol,urea and glycerin.

Suitable anti-foaming agents are silicones, long chain alcohols, andsalts of fatty acids.

Suitable colorants (e.g. in red, blue, or green) are pigments of lowwater solubility and water-soluble dyes. Examples are inorganiccolorants (e.g. iron oxide, titan oxide, iron hexacyanoferrate) andorganic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).

Suitable tackifiers or binders are polyvinylpyrrolidons,polyvinylacetates, polyvinyl alcohols, polyacrylates, biological orsynthetic waxes, and cellulose ethers.

Examples for composition types and their preparation are:

i) Water-soluble concentrates (SL, LS)10-60 wt % of a compound I according to the invention and 5-15 wt %wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/orin a water-soluble solvent (e.g. alcohols) ad 100 wt %. The activesubstance dissolves upon dilution with water.ii) Dispersible concentrates (DC)5-25 wt % of a compound I according to the invention and 1-10 wt %dispersant (e.g. polyvinylpyrrolidone) are dissolved in organic solvent(e.g. cyclohexanone) ad 100 wt %. Dilution with water gives adispersion.iii) Emulsifiable concentrates (EC)15-70 wt % of a compound I according to the invention and 5-10 wt %emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oilethoxylate) are dissolved in water-insoluble organic solvent (e.g.aromatic hydrocarbon) ad 100 wt %. Dilution with water gives anemulsion.

iv) Emulsions (EW, EO, ES)

5-40 wt % of a compound I according to the invention and 1-10 wt %emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oilethoxylate) are dissolved in 20-40 wt % water-insoluble organic solvent(e.g. aromatic hydrocarbon). This mixture is introduced into water ad100 wt % by means of an emulsifying machine and made into a homogeneousemulsion. Dilution with water gives an emulsion.

v) Suspensions (SC, OD, FS)

In an agitated ball mill, 20-60 wt % of a compound I according to theinvention are comminuted with addition of 2-10 wt % dispersants andwetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate),0,1-2 wt % thickener (e.g. xanthan gum) and water ad 100 wt % to give afine active substance suspension. Dilution with water gives a stablesuspension of the active substance. For FS type composition up to 40 wt% binder (e.g. polyvinylalcohol) is added.vi) Water-dispersible granules and water-soluble granules (WG, SG)50-80 wt % of a compound I according to the invention are ground finelywith addition of dispersants and wetting agents (e.g. sodiumlignosulfonate and alcohol ethoxylate) ad 100 wt % and prepared aswater-dispersible or water-soluble granules by means of technicalappliances (e.g. extrusion, spray tower, fluidized bed). Dilution withwater gives a stable dispersion or solution of the active substance.vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)50-80 wt % of a compound I according to the invention are ground in arotor-stator mill with addition of 1-5 wt % dispersants (e.g. sodiumlignosulfonate), 1-3 wt % wetting agents (e.g. alcohol ethoxylate) andsolid carrier (e.g. silica gel) ad 100 wt %. Dilution with water gives astable dispersion or solution of the active substance.viii) Gel (GW, GF)In an agitated ball mill, 5-25 wt % of a compound I according to theinvention are comminuted with addition of 3-10 wt % dispersants (e.g.sodium lignosulfonate), 1-5 wt % thickener (e.g. carboxymethylcellulose)and water ad 100 wt % to give a fine suspension of the active substance.Dilution with water gives a stable suspension of the active substance.

iv) Microemulsion (ME)

5-20 wt % of a compound I according to the invention are added to 5-30wt % organic solvent blend (e.g. fatty acid dimethylamide andcyclohexanone), 10-25 wt % surfactant blend (e.g. alkohol ethoxylate andarylphenol ethoxylate), and water ad 100%. This mixture is stirred for 1h to produce spontaneously a thermodynamically stable microemulsion.

iv) Microcapsules (CS)

An oil phase comprising 5-50 wt % of a compound I according to theinvention, 0-40 wt % water insoluble organic solvent (e.g. aromatichydrocarbon), 2-15 wt % acrylic monomers (e.g. methylmethacrylate,methacrylic acid and a di- or triacrylate) are dispersed into an aqueoussolution of a protective colloid (e.g. polyvinyl alcohol). Radicalpolymerization initiated by a radical initiator results in the formationof poly(meth)acrylate microcapsules. Alternatively, an oil phasecomprising 5-50 wt % of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), and anisocyanate monomer (e.g. diphenylmethene-4,4′-diisocyanatae) aredispersed into an aqueous solution of a protective colloid (e.g.polyvinyl alcohol). The addition of a polyamine (e.g.hexamethylenediamine) results in the formation of a polyureamicrocapsules. The monomers amount to 1-10 wt %. The wt % relate to thetotal CS composition.ix) Dustable powders (DP, DS)1-10 wt % of a compound I according to the invention are ground finelyand mixed intimately with solid carrier (e.g. finely divided kaolin) ad100 wt %.

x) Granules (GR, FG)

0.5-30 wt % of a compound I according to the invention is ground finelyand associated with solid carrier (e.g. silicate) ad 100 wt %.Granulation is achieved by extrusion, spray-drying or the fluidized bed.xi) Ultra-low volume liquids (UL)1-50 wt % of a compound I according to the invention are dissolved inorganic solvent (e.g. aromatic hydrocarbon) ad 100 wt %.

The compositions types i) to xi) may optionally comprise furtherauxiliaries, such as 0,1-1 wt % bactericides, 5-15 wt % anti-freezingagents, 0,1-1 wt % anti-foaming agents, and 0,1-1 wt % colorants.

The agrochemical compositions generally comprise between 0.01 and 95%,preferably between 0.1 and 90%, and in particular between 0.5 and 75%,by weight of active substance. The active substances are employed in apurity of from 90% to 100%, preferably from 95% to 100% (according toNMR spectrum).

Solutions for seed treamtent (LS), Suspoemulsions (SE), flowableconcentrates (FS), powders for dry treatment (DS), water-dispersiblepowders for slurry treatment (WS), water-soluble powders (SS), emulsions(ES), emulsifiable concentrates (EC) and gels (GF) are usually employedfor the purposes of treatment of plant propagation materials,particularly seeds. The compositions in question give, aftertwo-to-tenfold dilution, active substance concentrations of from 0.01 to60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-usepreparations. Application can be carried out before or during sowing.Methods for applying compound I and compositions thereof, respectively,on to plant propagation material, especially seeds include dressing,coating, pelleting, dusting, soaking and in-furrow application methodsof the propagation material. Preferably, compound I or the compositionsthereof, respectively, are applied on to the plant propagation materialby a method such that germination is not induced, e.g. by seed dressing,pelleting, coating and dusting.

When employed in plant protection, the amounts of active substancesapplied are, depending on the kind of effect desired, from 0.001 to 2 kgper ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05to 0.9 kg per ha, and in particular from 0.1 to 0.75 kg per ha.

In treatment of plant propagation materials such as seeds, e.g. bydusting, coating or drenching seed, amounts of active substance of from0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to100 g and most preferably from 5 to 100 g, per 100 kilogram of plantpropagation material (preferably seeds) are generally required.

When used in the protection of materials or stored products, the amountof active substance applied depends on the kind of application area andon the desired effect. Amounts customarily applied in the protection ofmaterials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of activesubstance per cubic meter of treated material.

Various types of oils, wetters, adjuvants, fertilizer, ormicronutrients, and further pesticides (e.g. herbicides, insecticides,fungicides, growth regulators, safeners) may be added to the activesubstances or the compositions comprising them as premix or, ifappropriate not until immediately prior to use (tank mix). These agentscan be admixed with the compositions according to the invention in aweight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

The user applies the composition according to the invention usually froma predosage device, a knapsack sprayer, a spray tank, a spray plane, oran irrigation system. Usually, the agrochemical composition is made upwith water, buffer, and/or further auxiliaries to the desiredapplication concentration and the ready-to-use spray liquor or theagrochemical composition according to the invention is thus obtained.Usually, 20 to 2000 liters, preferably 50 to 400 liters, of theready-to-use spray liquor are applied per hectare of agricultural usefularea.

According to one embodiment, individual components of the compositionaccording to the invention such as parts of a kit or parts of a binaryor ternary mixture may be mixed by the user himself in a spray tank andfurther auxiliaries may be added, if appropriate.

In a further embodiment, either individual components of the compositionaccording to the invention or partially premixed components, e.g.components comprising compounds I and/or active substances from thegroups M) or F) (see below), may be mixed by the user in a spray tankand further auxiliaries and additives may be added, if appropriate.

In a further embodiment, either individual components of the compositionaccording to the invention or partially premixed components, e. g.components comprising compounds I and/or active substances from thegroups M.1 to M.UN.X or F.I to F.XIII, can be applied jointly (e.g.after tank mix) or consecutively.

The following list M of pesticides, grouped according the Mode of ActionClassification of the Insecticide Resistance Action Committee (IRAC),together with which the compounds according to the invention can be usedand with which potential synergistic effects might be produced, isintended to illustrate the possible combinations, but not to impose anylimitation:

-   M.1 Acetylcholine esterase (AChE) inhibitors from the class of-   M.1A carbamates, for example aldicarb, alanycarb, bendiocarb,    benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran,    carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb,    isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb,    propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and    triazamate; or from the class of-   M.1B organophosphates, for example acephate, azamethiphos,    azinphos-ethyl, azinphosmethyl, cadusafos, chlorethoxyfos,    chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl,    coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/DDVP,    dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion,    ethoprophos, famphur, fenamiphos, fenitrothion, fenthion,    fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl    O-(methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion,    mecarbam, methamidophos, methidathion, mevinphos, monocrotophos,    naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl,    phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim,    pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos,    pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos,    terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon and    vamidothion;-   M.2. GABA-gated chloride channel antagonists such as:-   M.2A cyclodiene organochlorine compounds, as for example endosulfan    or chlordane; or-   M.2B fiproles (phenylpyrazoles), as for example ethiprole, fipronil,    flufiprole, pyrafluprole and pyriprole;-   M.3 Sodium channel modulators from the class of-   M.3A pyrethroids, for example acrinathrin, allethrin, d-cis-trans    allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin    S-cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin,    beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin,    cypermethrin, alpha-cypermethrin, beta-cypermethrin,    theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin,    empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate,    flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin,    meperfluthrin, metofluthrin, momfluorothrin, permethrin, phenothrin,    prallethrin, profluthrin, pyrethrin (pyrethrum), resmethrin,    silafluofen, tefluthrin, tetramethylfluthrin, tetramethrin,    tralomethrin and transfluthrin; or-   M.3B sodium channel modulators such as DDT or methoxychlor;-   M.4 Nicotinic acetylcholine receptor agonists (nAChR) from the class    of-   M.4A neonicotinoids, for example acteamiprid, chlothianidin,    dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam;    or the compounds-   M.4A.1:    1-[(6-chloro-3-pyridinyl)methyl]-2,3,5,6,7,8-hexahydro-9-nitro-(5S,8R)-5,8-Epoxy-1H-imidazo[1,2-a]azepine;    or-   M.4A.2:    1-[(6-chloro-3-pyridyl)methyl]-2-nitro-1-[(E)-pentylideneamino]guanidine;    or-   M4.A.3:    1-[(6-chloro-3-pyridyl)methyl]-7-methyl-8-nitro-5-propoxy-3,5,6,7-tetrahydro-2H-imidazo[1,2-a]pyridine;-   or M.4B nicotine.-   M.5 Nicotinic acetylcholine receptor allosteric activators from the    class of spinosyns, for example spinosad or spinetoram;-   M.6 Chloride channel activators from the class of avermectins and    milbemycins, for example abamectin, emamectin benzoate, ivermectin,    lepimectin or milbemectin;-   M.7 Juvenile hormone mimics, such as-   M.7A juvenile hormone analogues as hydroprene, kinoprene and    methoprene; or others as M.7B fenoxycarb or M.7C pyriproxyfen;-   M.8 miscellaneous non-specific (multi-site) inhibitors, for example-   M.8A alkyl halides as methyl bromide and other alkyl halides, or-   M.8B chloropicrin, or M.8C sulfuryl fluoride, or M.8D borax, or M.8E    tartar emetic;-   M.9 Selective homopteran feeding blockers, for example-   M.9B pymetrozine, or M.9C flonicamid;-   M.10 Mite growth inhibitors, for example-   M.10A clofentezine, hexythiazox and diflovidazin, or M.10B    etoxazole;-   M.11 Microbial disruptors of insect midgut membranes, for example    bacillus thuringiensis or bacillus sphaericus and the insecticidal    proteins they produce such as bacillus thuringiensis subsp.    israelensis, bacillus sphaericus, bacillus thuringiensis subsp.    aizawai, bacillus thuringiensis subsp. kurstaki and bacillus    thuringiensis subsp. tenebrionis, or the Bt crop proteins: Cry1Ab,    Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb and Cry34/35Ab1;-   M.12 Inhibitors of mitochondrial ATP synthase, for example-   M.12A diafenthiuron, or-   M.12B organotin miticides such as azocyclotin, cyhexatin or    fenbutatin oxide, or M.12C propargite, or M.12D tetradifon;-   M.13 Uncouplers of oxidative phosphorylation via disruption of the    proton gradient, for example chlorfenapyr, DNOC or sulfluramid;-   M.14 Nicotinic acetylcholine receptor (nAChR) channel blockers, for    example nereistoxin analogues as bensultap, cartap hydrochloride,    thiocyclam or thiosultap sodium;-   M.15 Inhibitors of the chitin biosynthesis type 0, such as    benzoylureas as for example bistrifluron, chlorfluazuron,    diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron,    novaluron, noviflumuron, teflubenzuron or triflumuron;-   M.16 Inhibitors of the chitin biosynthesis type 1, as for example    buprofezin;-   M.17 Moulting disruptors, Dipteran, as for example cyromazine;-   M.18 Ecdyson receptor agonists such as diacylhydrazines, for example    methoxyfenozide, tebufenozide, halofenozide, fufenozide or    chromafenozide;-   M.19 Octopamin receptor agonists, as for example amitraz;-   M.20 Mitochondrial complex III electron transport inhibitors, for    example-   M.20A hydramethylnon, or M.20B acequinocyl, or M.20C fluacrypyrim;-   M.21 Mitochondrial complex I electron transport inhibitors, for    example-   M.21A METI acaricides and insecticides such as fenazaquin,    fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad or tolfenpyrad,    or M.21B rotenone;-   M.22 Voltage-dependent sodium channel blockers, for example-   M.22A indoxacarb, or M.22B metaflumizone, or M.22C    1-[(E)-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]amino]-3-[4-(difluoromethoxy)phenyl]urea;-   M.23 Inhibitors of the of acetyl CoA carboxylase, such as Tetronic    and Tetramic acid derivatives, for example spirodiclofen,    spiromesifen or spirotetramat;-   M.24 Mitochondrial complex IV electron transport inhibitors, for    example-   M.24A phosphine such as aluminium phosphide, calcium phosphide,    phosphine or zinc phosphide, or M.24B cyanide.-   M.25 Mitochondrial complex II electron transport inhibitors, such as    beta-ketonitrile derivatives, for example cyenopyrafen or    cyflumetofen;-   M.28 Ryanodine receptor-modulators from the class of diamides, as    for example flubendiamide, chlorantraniliprole (Rynaxypyr®),    cyantraniliprole (Cyazypyr®), or the phthalamide compounds-   M.28.1:    (R)-3-Chlor-N1-{2-methyl-4-[1,2,2,2-tetrafluor-1-(trifluormethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamid    and-   M.28.2:    (S)-3-Chlor-N1-{2-methyl-4-[1,2,2,2-tetrafluor-1-(trifluormethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamid,    or the compound-   M.28.3:    3-bromo-N-{2-bromo-4-chloro-6-[(1-cyclopropylethyl)carbamoyl]phenyl}-1-(3-chlorpyridin-2-yl)-1H-pyrazole-5-carboxamide    (proposed ISO name: cyclaniliprole), or the compound-   M.28.4:    methyl-2-[3,5-dibromo-2-({[3-bromo-1-(3-chlorpyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-1,2-dimethylhydrazinecarboxylate;    or a compound selected from M.28.5a) to M.28.51):-   M.28.5a)    N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;-   M.28.5b)    N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazol    e-3-carboxamide;-   M.28.5c)    N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;-   M.28.5d)    N-[4,6-dichloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;-   M.28.5e)    N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(difluoromethyl)pyrazole-3-carboxamide;-   M.28.5f)    N-[4,6-dibromo-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;-   M.28.5g)    N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-cyano-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;-   M.28.5h)    N-[4,6-dibromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;-   M.28.5i)    N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methyl-phenyl]-5-bromo-2-(3-chloro-2-pyridyl)pyrazole-3-carboxamide;-   M.28.5j)    5-chloro-2-(3-chloro-2-pyridyl)-N-[2,4-dichloro-6-[(1-cyano-1-methyl-ethyl)carbamoyl]phenyl]pyrazole-3-carboxamide;-   M.28.5k)    5-bromo-N-[2,4-dichloro-6-(methylcarbamoyl)phenyl]-2-(3,5-dichloro-2-pyridyl)pyrazole-3-carboxamide;-   M.28.5l)    N-[2-(tert-butylcarbamoyl)-4-chloro-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(fluoromethoxy)pyrazole-3-carboxamide;    or a compound selected from-   M.28.6    N2-(1-cyano-1-methyl-ethyl)-N1-(2,4-dimethylphenyl)-3-iodo-phthalamide;    or-   M.28.7    3-chloro-N2-(1-cyano-1-methyl-ethyl)-N1-(2,4-dimethylphenyl)phthalamide;    M.UN.X insecticidal active compounds of unknown or uncertain mode of    action, as for example afidopyropen, azadirachtin, amidoflumet,    benzoximate, bifenazate, bromopropylate, chinomethionat, cryolite,    dicofol, flufenerim, flometoquin, fluensulfone, flupyradifurone,    piperonyl butoxide, pyridalyl, pyrifluquinazon, sulfoxaflor,    pyflubumide or the compounds-   M.UN.X.1:    4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-N-[(2,2,2-trifluoro-ethylcarbamoyl)-methyl]-benzamide,    or the compound-   M.UN.X.2:    4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]naphthalene-1-carboxamide,    or the compound-   M.UN.X.3:    11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]-tetradec-11-en-10-one,    or the compound-   M.UN.X.4:    3-(4′-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one,    or the compound-   M.UN.X.5:    1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine,    or actives on basis of bacillus firmus (Votivo, 1-1582); or-   M.UN.X.6; a compound selected from the group of-   M.UN.X.6a)    (E/Z)-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide;-   M.UN.X.6b)    (E/Z)-N-[1-[(6-chloro-5-fluoro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide;-   M.UN.X.6c)    (E/Z)-2,2,2-trifluoro-N-[1-[(6-fluoro-3-pyridyl)methyl]-2-pyridylidene]acetamide;-   M.UN.X.6d)    (E/Z)-N-[1-[(6-bromo-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide;-   M.UN.X.6e)    (E/Z)-N-[1-[1-(6-chloro-3-pyridyl)ethyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide;-   M.UN.X.6f)    (E/Z)-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoro-acetamide;-   M.UN.X.6g)    (E/Z)-2-chloro-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoro-acetamide;-   M.UN.X.6h)    (E/Z)-N-[1-[(2-chloropyrimidin-5-yl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide    and-   M.UN.X.6i)    (E/Z)-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,3,3,3-pentafluoro-propanamide.);    or of the compounds-   M.UN.X.7:    3-[3-chloro-5-(trifluoromethyl)phenyl]-4-oxo-1-(pyrimidin-5-ylmethyl)pyrido[1,2-a]pyrimidin-1-ium-2-olate;    or-   M.UN.X.8:    1-[(2-chlorothiazol-5-yl)methyl]-3-(3,5-dichlorophenyl)-9-methyl-4-oxo-pyrido[1,2-a]pyrimidin-1-ium-2-olate;    or M.UN.X.9:    8-chloro-N-[2-chloro-5-methoxyphenyl)sulfonyl]-6-trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide;    or M.UN.X.10:    4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide;    or-   M.UN.X.11:    5-[3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1H-pyrazole.

The commercially available compounds of the group M listed above may befound in The Pesticide Manual, 15th Edition, C. D. S. Tomlin, BritishCrop Protection Council (2011) among other publications.

The quinoline derivative flometoquin is shown in WO2006/013896. Theaminofuranone compounds flupyradifurone is known from WO 2007/115644.The sulfoximine compound sulfoxaflor is known from WO2007/149134. Thepyrethroid momfluorothrin is known from U.S. Pat. No. 6,908,945. Thepyrazole acaricide pyflubumide is known from WO2007/020986. Theisoxazoline compounds have been described likewise M.UN.X.1 inWO2005/085216, M.UN.X2. in WO2009/002809 and in WO2011/149749 and theisoxazoline M.UN.X.10 in WO2013/050317. The pyripyropene derivativeafidopyropen has been described in WO 2006/129714. Thespiroketal-substituted cyclic ketoenol derivative M.UN.X.3 is known fromWO2006/089633 and the biphenyl-substituted spirocyclic ketoenolderivative M.UN.X.4 from WO2008/067911. Finally triazoylphenylsulfidelike M.UN.X.5 have been described in WO2006/043635 and biologicalcontrol agents on basis of bacillus firmus in WO2009/124707. Theneonicotionids 4A.1 is known from WO20120/069266 and WO2011/06946, theM.4.A.2 from WO2013/003977, the M4.A.3. from WO2010/069266.

The Metaflumizone analogue M.22C is described in CN 10171577. Thephthalamides M.28.1 and M.28.2 are both known from WO 2007/101540. Theanthranilamide M.28.3 has been described in WO2005/077934. The hydrazidecompound M.28.4 has been described in WO 2007/043677. Theanthranilamides M.28.5a) to M.28.5h) can be prepared as described in WO2007/006670, WO2013/024009 and WO2013/024010, the anthranilamideM.28.5i) is described in WO2011/085575, the M.28.5j) in WO2008/134969,the M.28.5k) in US2011/046186 and the M.28.51) in WO2012/034403. Thediamide compounds M.28.6 and M.28.7 can be found in CN102613183.

The compounds M.UN.X.6a) to M.UN.X.6i) listed in M.UN.X.6 have beendescribed in WO2012/029672. The mesoionic antagonist compound M.UN.X.7was described in WO2012/092115, the mesoionic antagonist compoundM.UN.X.8 was described in WO 2013/192035, the nematicide M.UN.X.9 inWO2013/055584 and the pyridalyl-type analogue M.UN.X.11 inWO2010/060379.

Preferred additional pesticidally active ingredients are those selectedfrom the IRAC group 1, the Acetylcholinesterase (AChE) inhibitors,herein from the group 1A (Carbamtes) Thiodicarb, Methomyl and Carbaryl,and from the group 1B(Organophosphates), especially Acephate,Chlorpyriphos and Dimethoate, from the group 2B, the fiproles, hereespecially ethiprole and fipronil, from the group 3, the pyrethroids,here especially lambda-cyhalothrin, alpha-cypermethrin or deltametrin,and from the group 4A, the neonicotinoids, here especially acetamiprid,clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid orthiomethoxam.

Especially combinations of compounds of the invention with fiproles,neonictinoids or pyrethroids may possibly exhibit synergistic control ofstinkbugs (according to the Colby formula), in particular Euschistus,e.g. Euschistus heros.

The following list F of active substances, in conjunction with which thecompounds according to the invention can be used, is intended toillustrate the possible combinations but does not limit them:

-   F.I) Respiration inhibitors    -   F.I 1) Inhibitors of complex III at Q_(o) site (e.g.        strobilurins): azoxystrobin, coumethoxystrobin, coumoxystrobin,        dimoxystrobin, enestroburin, fenaminstrobin,        fenoxystrobin/flufenoxystrobin, fluoxastrobin, kresoxim-methyl,        mandestrobine, metominostrobin, orysastrobin, picoxystrobin,        pyraclostrobin, pyrametostrobin, pyraoxystrobin, trifloxystrobin        and        2-(2-(3-(2,6-di-chlorophenyl)-1-methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N-methyl-acetamide,        pyribencarb, triclopyricarb/chlorodincarb, famoxadone,        fenamidone;    -   F.I 2) inhibitors of complex III at Q_(i) site: cyazofamid,        amisulbrom,        [(3S,6S,7R,8R)-8-benzyl-3-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]        2-methylpropanoate,        [(3S,6S,7R,8R)-8-benzyl-3-[[3-(acetoxymethoxy)-4-methoxy-pyridine-2-carbonyl]amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]        2-methylpropanoate,        [(3S,6S,7R,8R)-8-benzyl-3-[(3-isobutoxycarbonyloxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]        2-methylpropanoate,        [(3S,6S,7R,8R)-8-benzyl-3-[[3-(1,3-benzodioxol-5-ylmethoxy)-4-methoxy-pyridine-2-carbonyl]amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]        2-methylpropanoate;        (3S,6S,7R,8R)-3-[[(3-hydroxy-4-methoxy-2-pyridinyl)carbonyl]amino]-6-methyl-4,9-dioxo-8-(phenylmethyl)-1,5-dioxonan-7-yl        2-methylpropanoate;    -   F.I 3) inhibitors of complex II (e. g. carboxamides): benodanil,        benzovindiflupyr, bixafen, boscalid, carboxin, fenfuram,        fluopyram, flutolanil, fluxapyroxad, furametpyr, isofetamid,        isopyrazam, mepronil, oxycarboxin, penflufen, penthiopyrad,        sedaxane, tecloftalam, thifluzamide,        N-(4′-trifluoromethylthiobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide,        N-(2-(1,3,3-trimethyl-butyl)-phenyl)-1,3-dimethyl-5-fluoro-1H-pyrazole-4-carboxamide,        3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,        3-(trifluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,        1,3-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,        3-(trifluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,        1,3,5-trimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,        N-(7-fluoro-1,1,3-trimethylindan-4-yl)-1,3-dimethyl-pyrazole-4-carboxamide,        N-[2-(2,4-dichlorophenyl)-2-methoxy-1-methyl-ethyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide,        N-[2-(2,4-difluorophenyl)phenyl]-3-(trifluoromethyl)pyrazine-2-carboxamide;    -   F.I 4) other respiration inhibitors (e.g. complex I,        uncouplers): diflumetorim,        (5,8-difluoroquinazolin-4-yl)-{2-[2-fluoro-4-(4-trifluoromethyl        pyridin-2-yloxy)-phenyl]-ethyl}-amine; nitrophenyl derivates:        binapacryl, dinobuton, dinocap, fluazinam; ferimzone;        organometal compounds: fentin salts, such as fentin-acetate,        fentin chloride or fentin hydroxide; ametoctradin; and        silthiofam;-   F.II) Sterol biosynthesis inhibitors (SBI fungicides)    -   F.II 1) C14 demethylase inhibitors (DMI fungicides): triazoles:        azaconazole, bitertanol, bromuconazole, cyproconazole,        difenoconazole, diniconazole, diniconazole-M, epoxiconazole,        fenbuconazole, fluquinconazole, flusilazole, flutriafol,        hexaconazole, imibenconazole, ipconazole, metconazole,        myclobutanil, oxpoconazole, paclobutrazole, penconazole,        propiconazole, prothioconazole, simeconazole, tebuconazole,        tetraconazole, triadimefon, triadimenol, triticonazole,        uniconazole, 1-[rel-(2S;        3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-5-thio-cyanato-1H-[1,2,4]triazole,        2-[rel-(2S,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-2H-[1,2,4]triazole-3-thiol,        2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)pentan-2-ol,        1-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-cyclopropyl-2-(1,2,4-triazol-1-yl)ethanol,        2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)butan-2-ol,        2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)butan-2-ol,        2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol,        2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol,        2-[2-chloro-4-(4-chlorophenoxy)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol,        2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)pentan-2-ol,        2-[4-(4-fluorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol;        imidazoles: imazalil, pefurazoate, prochloraz, triflumizol;        pyrimidines, pyridines and piperazines: fenarimol, nuarimol,        pyrifenox, triforine,        [3-(4-chloro-2-fluoro-phenyl)-5-(2,4-difluorophenyl)isoxazol-4-yl]-(3-pyridyl)methanol;        F.II 2) Delta14-reductase inhibitors: aldimorph, dodemorph,        dodemorph-acetate, fenpropimorph, tridemorph, fenpropidin,        piperalin, spiroxamine; F.II 3) Inhibitors of 3-keto reductase:        fenhexamid;-   F.III) Nucleic acid synthesis inhibitors    -   F.III 1) phenylamides or acyl amino acid fungicides: benalaxyl,        benalaxyl-M, kiralaxyl, metalaxyl, metalaxyl-M (mefenoxam),        ofurace, oxadixyl;    -   F.III 2) others: hymexazole, octhilinone, oxolinic acid,        bupirimate, 5-fluorocytosine,        5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine,        5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine;-   F.IV) Inhibitors of cell division and cytoskeleton    -   F.IV 1) tubulin inhibitors, such as benzimidazoles,        thiophanates: benomyl, carbendazim, fuberidazole, thiabendazole,        thiophanate-methyl; triazolopyrimidines:        5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;        F.IV 2) other cell division inhibitors: diethofencarb,        ethaboxam, pencycuron, fluopicolide, zoxamide, metrafenone,        pyriofenone;-   F.V) Inhibitors of amino acid and protein synthesis    -   F.V 1) methionine synthesis inhibitors (anilino-pyrimidines):        cyprodinil, mepanipyrim, pyrimethanil;    -   F.V 2) protein synthesis inhibitors: blasticidin-S, kasugamycin,        kasugamycin hydrochloride-hydrate, mildiomycin, streptomycin,        oxytetracyclin, polyoxine, validamycin A;-   F.VI) Signal transduction inhibitors    -   F.VI 1) MAP/histidine kinase inhibitors: fluoroimid, iprodione,        procymidone, vinclozolin, fenpiclonil, fludioxonil;    -   F.VI 2) G protein inhibitors: quinoxyfen;-   F.VII) Lipid and membrane synthesis inhibitors    -   F.VII 1) Phospholipid biosynthesis inhibitors: edifenphos,        iprobenfos, pyrazophos, isoprothiolane;    -   F.VII 2) lipid peroxidation: dicloran, quintozene, tecnazene,        tolclofos-methyl, biphenyl, chloroneb, etridiazole;    -   F.VII 3) phospholipid biosynthesis and cell wall deposition:        dimethomorph, flumorph, mandipropamid, pyrimorph,        benthiavalicarb, iprovalicarb, valifenalate and        N-(1-(1-(4-cyano-phenyl)ethanesulfonyl)-but-2-yl) carbamic        acid-(4-fluorophenyl) ester;    -   F.VII 4) compounds affecting cell membrane permeability and        fatty acides: propamocarb, propamocarb-hydrochlorid;    -   F.VII 5) fatty acid amide hydrolase inhibitors: oxathiapiprolin;-   F.VIII) Inhibitors with Multi Site Action    -   F.VIII 1) inorganic active substances: Bordeaux mixture, copper        acetate, copper hydroxide, copper oxychloride, basic copper        sulfate, sulfur;    -   F.VIII 2) thio- and dithiocarbamates: ferbam, mancozeb, maneb,        metam, metiram, propineb, thiram, zineb, ziram;    -   F.VIII 3) organochlorine compounds (e.g. phthalimides,        sulfamides, chloronitriles): anilazine, chlorothalonil,        captafol, captan, folpet, dichlofluanid, dichlorophen,        hexachlorobenzene, pentachlorphenole and its salts, phthalide,        tolylfluanid,        N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl-benzenesulfonamide;    -   F.VIII 4) guanidines and others: guanidine, dodine, dodine free        base, guazatine, guazatine-acetate, iminoctadine,        iminoctadine-triacetate, iminoctadine-tris(albesilate),        dithianon,        2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetraone;-   F.IX) Cell wall synthesis inhibitors    -   F.IX 1) inhibitors of glucan synthesis: validamycin, polyoxin B;    -   F.IX 2) melanin synthesis inhibitors: pyroquilon, tricyclazole,        carpropamid, dicyclomet, fenoxanil;-   F.X) Plant defence inducers    -   F.X 1) acibenzolar-S-methyl, probenazole, isotianil, tiadinil,        prohexadione-calcium;    -   F.X 2) phosphonates: fosetyl, fosetyl-aluminum, phosphorous acid        and its salts,        4-cyclopropyl-N-(2,4-dimethoxyphenyl)thiadiazole-5-carboxamide;-   F.XI) Unknown mode of action bronopol, chinomethionat, cyflufenamid,    cymoxanil, dazomet, debacarb, diclo-mezine, difenzoquat,    difenzoquat-methylsulfate, diphenylamin, fenpyrazamine, flumetover,    flusulfamide, flutianil, methasulfocarb, nitrapyrin,    nitrothal-isopropyl, oxathiapiprolin, picarbutrazox, tolprocarb,    2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,    2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,    2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chloro-6-(prop-2-yn-1-yl-oxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,    oxin-copper, proquinazid, tebufloquin, tecloftalam, triazoxide,    2-butoxy-6-iodo-3-propylchromen-4-one,    N-(cyclopropylmethoxyimino-(6-difluoro-methoxy-2,3-difluoro-phenyl)-methyl)-2-phenyl    acetamide,    N′-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl    formamidine,    N′-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl    formamidine,    N′-(2-methyl-5-trifluoromethyl-4-(3-trimethyl-silanyl-propoxy)-phenyl)-N-ethyl-N-methyl    formamidine,    N′-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl    formamidine, methoxy-acetic acid    6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl ester,    3-[5-(4-methylphenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine,    3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine    (pyrisoxazole), N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic    acid amide,    5-chloro-1-(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1H-benzoimidazole,    2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide,    ethyl (Z)-3-amino-2-cyano-3-phenyl-prop-2-enoate, pentyl    N-[6-[[(Z)-[(1-methyltetra-zol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate,    2-[2-[(7,8-difluoro-2-methyl-3-quinolyl)oxy]-6-fluoro-phenyl]propan-2-ol,    2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol,    3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline,    3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline,    3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline;-   F.XII) Biopesticides    -   F.XII 1) Microbial pesticides with fungicidal, bactericidal,        viricidal and/or plant defense activator activity: Ampelomyces        quisqualis, Aspergillus flavus, Aureobasidium pullulans,        Bacillus amyloliquefaciens, B. mojavensis, B. pumilus, B.        simplex, B. solisalsi, B. subtilis, B. subtilis var.        amyloliquefaciens, Candida oleophila, C. saitoana, Clavibacter        michiganensis (bacteriophages), Coniothyrium minitans,        Cryphonectria parasitica, Cryptococcus albidus, Dilophosphora        alopecuri, Fusarium oxysporum, Clonostachys rosea f. catenulate        (also named Gliocladium catenulatum), Gliocladium roseum,        Lysobacter antibioticus, L. enzymogenes, Metschnikowia        fructicola, Microdochium dimerum, Microsphaeropsis ochracea,        Muscodor albus, Paenibacillus polymyxa, Pantoea vagans,        Phlebiopsis gigantea, Pseudomonas sp., Pseudomonas chloraphis,        Pseudozyma flocculosa, Pichia anomala, Pythium oligandrum,        Sphaerodes mycoparasitica, Streptomyces griseoviridis, S.        lydicus, S. violaceusniger, Talaromyces flavus, Trichoderma        asperellum, T. atroviride, T. fertile, T. gamsii, T.        harmatum, T. harzianum; mixture of T. harzianum and T. viride;        mixture of T. polysporum and T. harzianum; T. stromaticum, T.        virens (also named Gliocladium virens), T. viride, Typhula        phacorrhiza, Ulocladium oudemansii, Verticillium dahlia,        zucchini yellow mosaic virus (avirulent strain);    -   F.XII 2) Biochemical pesticides with fungicidal, bactericidal,        viricidal and/or plant defense activator activity: chitosan        (hydrolysate), harpin protein, laminarin, Menhaden fish oil,        natamycin, Plum pox virus coat protein, potassium or sodium        bicarbonate, Reynoutria sachlinensis extract, salicylic acid,        tea tree oil;

The fungicidal active compounds mentioned above of groups F.I to F.XI,their preparation and their action against harmful fungi are generallyknown (cf., for example, http://www.hclrss.demon.co.uk/index.html).

The fungicides of chemical nature described by common names, theirpreparation and their activity against pests are known (cf.:http://www.alanwood.net/pesticides/); these pesticides are oftencommercially available.

The fungicides described by IUPAC nomenclature, their preparation andtheir pesticidal activity are also known (cf. Can. J. Plant Sci. 48(6),587-94, 1968; EP-A 141 317; EP-A 152 031; EP-A 226 917; EP-A 243 970;EP-A 256 503; EP-A 428 941; EP-A 532 022; EP-A 1 028 125; EP-A 1 035122; EP-A 1 201 648; EP-A 1 122 244, JP 2002316902; DE 19650197; DE10021412; DE 102005009458; U.S. Pat. No. 3,296,272; U.S. Pat. No.3,325,503; WO 98/46608; WO 99/14187; WO 99/24413; WO 99/27783; WO00/29404; WO 00/46148; WO 00/65913; WO 01/54501; WO 01/56358; WO02/22583; WO 02/40431; WO 03/10149; WO 03/11853; WO 03/14103; WO03/16286; WO 03/53145; WO 03/61388; WO 03/66609; WO 03/74491; WO04/49804; WO 04/83193; WO 05/120234; WO 05/123689; WO 05/123690; WO05/63721; WO 05/87772; WO 05/87773; WO 06/15866; WO 06/87325; WO06/87343; WO 07/82098; WO 07/90624, WO 11/028657, WO2012/168188, WO2007/006670, WO 11/77514; WO13/047749, WO 10/069882, WO 13/047441, WO03/16303, WO 09/90181, WO 13/007767, WO 13/010862, WO 13/024009 and WO13/024010).

The biopesticides from group F.XII) of fungicides, their preparation andtheir pesticidal activity e.g. against harmful fungi or insects areknown (e-Pesticide Manual V 5.2 (ISBN 978 1 901396 85 0) (2008-2011);http://www.epa.gov/opp00001/biopesticides/, see product lists therein;http://www.omri.org/omri-lists, see lists therein; Bio-PesticidesDatabase BPDB http://sitem.herts.ac.uk/aeru/bpdb/, see A to Z linktherein).

The biopesticides from group F.XII. may also have insecticidal,acaricidal, molluscidal, pheromone, nematicidal, plant stress reducing,plant growth regulator, plant growth promoting and/or yield enhancingactivity. The biopesticides from group L3) and/or L4) may also havefungicidal, bactericidal, viricidal, plant defense activator, plantstress reducing, plant growth regulator, plant growth promoting and/oryield enhancing activity. The biopesticides from group F.XII may alsohave fungicidal, bactericidal, viricidal, plant defense activator,insecticidal, acaricidal, molluscidal, pheromone and/or nematicidalactivity.

Many of these biopesticides are registered and/or are commerciallyavailable: aluminium silicate (Screen™ Duo from Certis LLC, USA),Agrobacterium radio-bacter K1026 (e.g. NoGall® from Becker Underwood PtyLtd., Australia), A. radiobacter K84 (Nature 280, 697-699, 1979; e.g.GallTroll® from AG Biochem, Inc., C, USA), Ampelomyces quisqualis M-10(e.g. AQ 10® from Intrachem Bio GmbH & Co. KG, Germany), Ascophyllumnodosum (Norwegian kelp, Brown kelp) extract or filtrate (e.g. ORKA GOLDfrom Becker Underwood, South Africa; or Goemar® from LaboratoiresGoemar, France), Aspergillus flavus NRRL 21882 isolated from a peanut inGeorgia in 1991 by the USDA, National Peanut Research Laboratory (e.g.in Afla-Guard® from Syngenta, CH), mixtures of Aureobasidium pullulansDSM14940 and DSM14941 (e.g. blastospores in BlossomProtect® frombio-ferm GmbH, Germany), Azospirillum brasilense XOH (e.g. AZOS fromXtreme Gardening, USA or RTI Reforestation Technologies International;USA), Bacillus amyloliquefaciens FZB42 (e.g. in RhizoVital® 42 fromAbiTEP GmbH, Berlin, Germany), B. amyloliquefaciens IN937a (J.Microbiol. Biotechnol. 17(2), 280-286, 2007; e.g. in BioYield® fromGustafson LLC, TX, USA), B. amyloliquefaciens IT-45 (CNCM 1-3800) (e.g.Rhizocell C from ITHEC, France), B. amyloliquefaciens subsp. plantarumMBI600 (NRRL B-50595, deposited at United States Department ofAgriculture) (e.g. Integral®, Subtilex® NG from Becker Underwood, USA),B. cereus CNCM 1-1562 (U.S. Pat. No. 6,406,690), B. firmus CNCM 1-1582(WO 2009/126473, WO 2009/124707, U.S. Pat. No. 6,406,690; Votivo® fromBayer Crop Science LP, USA), B. pumilus GB34 (ATCC 700814; e.g. inYieldShield® from Gustafson LLC, TX, USA), and Bacillus pumilus KFP9F(NRRL B-50754) (e.g. in BAC-UP or FUSION-P from Becker Underwood SouthAfrica), B. pumilus QST 2808 (NRRL B-30087) (e.g. Sonata® and Ballad®Plus from AgraQuest Inc., USA), B. subtilis GB03 (e.g. Kodiak® orBioYield® from Gustafson, Inc., USA; or Companion® from Growth Products,Ltd., White Plains, N.Y. 10603, USA), B. subtilis GB07 (Epic® fromGustafson, Inc., USA), B. subtilis QST-713 (NRRL B-21661 in Rhapsody®,Serenade® MAX and Serenade® ASO from AgraQuest Inc., USA), B. subtilisvar. amylolique-faciens FZB24 (e.g. Taegro® from Novozyme Biologicals,Inc., USA), B. subtilis var. amyloliquefaciens D747 (e.g. Double Nickel55 from Certis LLC, USA), B. thuringiensis ssp. aizawai ABTS-1857 (e.g.in XenTari® from BioFa AG, Münsingen, Germany), B. t. ssp. aizawai SAN401 I, ABG-6305 and ABG-6346, Bacillus t. ssp. israelensis AM65-52 (e.g.in VectoBac® from Valent BioSciences, IL, USA), Bacillus thuringiensisssp. kurstaki SB4 (NRRL B-50753; e.g. Beta Pro® from Becker Underwood,South Africa), B. t. ssp. kurstaki ABTS-351 identical to HD-1 (ATCCSD-1275; e.g. in Dipel® DF from Valent BioSciences, IL, USA), B. t. ssp.kurstaki EG 2348 (e.g. in Lepinox® or Rapax® from CBC (Europe) S.r.l.,Italy), B. t. ssp. tenebrionis DSM 2803 (EP 0 585 215 B1; identical toNRRL B-15939; Mycogen Corp.), B. t. ssp. tenebrionis NB-125 (DSM 5526;EP 0 585 215 B1; also referred to as SAN 418 I or ABG-6479; formerproduction strain of Novo-Nordisk), B. t. ssp. tenebrionis NB-176 (orNB-176-1) a gamma-irridated, induced high-yielding mutant of strainNB-125 (DSM 5480; EP 585 215 B1; Novodor® from Valent BioSciences,Switzerland), Beauveria bassiana ATCC 74040 (e.g. in Naturalis® from CBC(Europe) S.r.l., Italy), B. bassiana DSM 12256 (US 200020031495; e.g.BioExpert® SC from Live Systems Technology S.A., Colombia), B. bassianaGHA (BotaniGard® 22WGP from Laverlam Int. Corp., USA), B. bassiana PPRI5339 (ARSEF number 5339 in the USDA ARS collection of entomopathogenicfungal cultures; NRRL 50757) (e.g. BroadBand® from Becker Underwood,South Africa), B. brongniartii (e.g. in Melocont® from Agrifutur,Agrianello, Italy, for control of cockchafer; J. Appl. Microbiol.100(5), 1063-72, 2006), Bradyrhizobium sp. (e.g. Vault® from BeckerUnderwood, USA), B. japonicum (e.g. VAULT® from Becker Underwood, USA),Candida oleophila 1-182 (NRRL Y-18846; e.g. Aspire® from Ecogen Inc.,USA, Phytoparasitica 23(3), 231-234, 1995), C. oleophila strain O (NRRLY-2317; Biological Control 51, 403-408, 2009), Candida saitoana (e.g.Biocure® (in mixture with lysozyme) and BioCoat® from Micro Flo Company,USA (BASF SE) and Arysta), Chitosan (e.g. Armour-Zen® from BotriZenLtd., NZ), Clonostachys rosea f. catenulata, also named Gliocladiumcatenulatum (e.g. isolate J 1446: Prestop® from Verdera Oy, Finland),Chromobacterium subtsugae PRAA4-1 isolated from soil under an easternhemlock (Tsuga canadensis) in the Catoctin Mountain region of centralMaryland (e.g. in GRANDEVO from Marrone Bio Innovations, USA),Coniothyrium minitans CON/M/91-08 (e.g. Contans® WG from Prophyta,Germany), Cryphonectria parasitica (e.g. Endothia parasitica from CNICM,France), Cryptococcus albidus (e.g. YIELD PLUS® from AnchorBio-Technologies, South Africa), Cryptophlebia leucotreta granulovirus(CrleGV) (e.g. in CRYPTEX from Adermatt Biocontrol, Switzerland), Cydiapomonella granulovirus (CpGV) V03 (DSM GV-0006; e.g. in MADEX Max fromAndermatt Biocontrol, Switzerland), CpGV V22 (DSM GV-0014; e.g. in MADEXTwin from Adermatt Biocontrol, Switzerland), Delftia acidovorans RAY209(ATCC PTA-4249; WO 2003/57861; e.g. in BIOBOOST from Brett Young,Winnipeg, Canada), Dilophosphora alopecuri (Twist Fungus from BeckerUnderwood, Australia), Ecklonia maxima (kelp) extract (e.g. KELPAK SLfrom Kelp Products Ltd, South Africa), formononetin (e.g. in MYCONATEfrom Plant Health Care plc, U.K.), Fusarium oxysporum (e.g. BIOFOX® fromS.I.A.P.A., Italy, FUSACLEAN® from Natural Plant Protection, France),Glomus intraradices (e.g. MYC 4000 from ITHEC, France), Glomusintraradices RTI-801 (e.g. MYKOS from Xtreme Gardening, USA or RTIReforestation Technologies International; USA), grapefruit seeds andpulp extract (e.g. BC-1000 from Chemie S.A., Chile), harpin (alpha-beta)protein (e.g. MESSENGER or HARP—N-Tek from Plant Health Care plc, U.K.;Science 257, 1-132, 1992), Heterorhabditis bacteriophaga (e.g. Nemasys®G from Becker Underwood Ltd., UK), Isaria fumosorosea Apopka-97 (ATCC20874) (PFR-97™ from Certis LLC, USA), cis-jasmone (U.S. Pat. No.8,221,736), laminarin (e.g. in VACCIPLANT from Laboratoires Goemar, St.Malo, France or Stahler S A, Switzerland), Lecanicillium longisporumKV42 and KV71 (e.g. VERTALEC® from Koppert BV, Netherlands), L.muscarium KV01 (formerly Verticillium lecanii) (e.g. MYCOTAL fromKoppert BV, Netherlands), Lysobacter antibioticus 13-1 (BiologicalControl 45, 288-296, 2008), L. antibioticus HS124 (Curr. Microbiol.59(6), 608-615, 2009), L. enzymogenes 3.1T8 (Microbiol. Res. 158,107-115; Biological Control 31(2), 145-154, 2004), Metarhiziumanisopliae var. acridum IMI 330189 (isolated from Ornithacris cavroisiin Niger; also NRRL 50758) (e.g. GREEN MUSCLE® from Becker Underwood,South Africa), M. a. var. acridum FI-985 (e.g. GREEN GUARD® SC fromBecker Underwood Pty Ltd, Australia), M. anisopliae FI-1045 (e.g.BIOCANE® from Becker Underwood Pty Ltd, Australia), M. anisopliae F52(DSM 3884, ATCC 90448; e.g. MET52® Novozymes Biologicals BioAg Group,Canada), M. anisopliae ICIPE 69 (e.g. METATHRIPOL from ICIPE, Nairobe,Kenya), Metschnikowia fructicola (NRRL Y-30752; e.g. SH EM ER® fromAgrogreen, Israel, now distributed by Bayer CropSciences, Germany; U.S.Pat. No. 6,994,849), Microdochium dimerum (e.g. ANTIBOT® from Agrauxine,France), Microsphaeropsis ochracea P130A (ATCC 74412 isolated from appleleaves from an abandoned orchard, St-Joseph-du-Lac, Quebec, Canada in1993; Mycologia 94(2), 297-301, 2002), Muscodor albus QST 20799originally isolated from the bark of a cinnamon tree in Honduras (e.g.in development products Muscudor™ or QRD300 from AgraQuest, USA), Neemoil (e.g. TRILOGY®, TRIACT® 70 EC from Certis LLC, USA), Nomuraea rileyistrains SA86101, GU87401, SR86151, CG128 and VA9101, Paecilomycesfumosoroseus FE 9901 (e.g. NO FLY™ from Natural Industries, Inc., USA),P. lilacinus 251 (e.g. in BioAct®/MeloCon® from Prophyta, Germany; CropProtection 27, 352-361, 2008; originally isolated from infected nematodeeggs in the Philippines), P. lilacinus DSM 15169 (e.g. NEMATA® SC fromLive Systems Technology S.A., Colombia), P. lilacinus BCP2 (NRRL 50756;e.g. PL GOLD from Becker Underwood BioAg SA Ltd, South Africa), mixtureof Paenibacillus alvei NAS6G6 (NRRL B-50755), Pantoea vagans (formerlyagglomerans) C9-1 (originally isolated in 1994 from apple stem tissue;BlightBan C9-1® from NuFrams America Inc., USA, for control of fireblight in apple; J. Bacteriol. 192(24) 6486-6487, 2010), Pasteuria spp.ATCC PTA-9643 (WO 2010/085795), Pasteuria spp. ATCC SD-5832 (WO2012/064527), P. nishizawae (WO 2010/80169), P. penetrans (U.S. Pat. No.5,248,500), P. ramose (WO 2010/80619), P. thornea (WO 2010/80169), P.usgae (WO 2010/80169), Penicillium bilaiae (e.g. Jump Start® fromNovozymes Biologicals BioAg Group, Canada, originally isolated from soilin southern Alberta; Fertilizer Res. 39, 97-103, 1994), Phlebiopsisgigantea (e.g. RotStop® from Verdera Oy, Finland), Pichia anomalaWRL-076 (NRRL Y-30842; U.S. Pat. No. 8,206,972), potassium bicarbonate(e.g. Amicarb® from Stähler SA, Switzerland), potassium silicate (e.g.Sil-MATRIX™ from Certis LLC, USA), Pseudozyma flocculosa PF-A22 UL (e.g.Sporodex® from Plant Products Co. Ltd., Canada), Pseudomonas sp. DSM13134 (WO 2001/40441, e.g. in PRORADIX from Sourcon Padena GmbH & Co.KG, Hechinger Str. 262, 72072 Tibingen, Germany), P. chloraphis MA 342(e.g. in CERALL or CEDEMON from BioAgri AB, Uppsala, Sweden), P.fluorescens CL 145A (e.g. in ZEQUANOX from Marrone Biolnnovations,Davis, Calif., USA; J. Invertebr. Pathol. 113(1):104-14, 2013), Pythiumoligandrum DV 74 (ATCC 38472; e.g. POLYVERSUM® from Remeslo SSRO,Biopreparaty, Czech Rep. and GOWAN, USA; US 2013/0035230), Reynoutriasachlinensis extract (e.g. REGALIA® SC from Marrone Biolnnovations,Davis, Calif., USA), Rhizobium leguminosarum bv. phaseolii (e.g.RHIZO-STICK from Becker Underwood, USA), R. l. trifolii RP113-7 (e.g.DORMAL from Becker Underwood, USA; Appl. Environ. Microbiol. 44(5),1096-1101), R. l. bv. viciae P1N P3Cst (also referred to as 1435; NewPhytol 179(1), 224-235, 2008; e.g. in NODULATOR PL Peat Granule fromBecker Underwood, USA; or in NODULATOR XL PL bfrom Becker Underwood,Canada), R. l. bv. viciae SU303 (e.g. NODULAID Group E from BeckerUnderwood, Australia), R. l. bv. viciae WSM1455 (e.g. NODULAID Group Ffrom Becker Underwood, Australia), R. tropici SEMIA 4080 (identical toPRF 81; Soil Biology & Biochemistry 39, 867-876, 2007), Sinorhizobiummeliloti MSDJ0848 (INRA, France) also referred to as strain 2011 orRCR2011 (Mol Gen Genomics (2004) 272: 1-17; e.g. DORMAL ALFALFA fromBecker Underwood, USA; NITRAGIN® Gold from Novozymes Biologicals BioAgGroup, Canada), Sphaerodes mycoparasitica IDAC 301008-01 (WO2011/022809), Steinernema carpocapsae (e.g. MILLENIUM® from BeckerUnderwood Ltd., UK), S. feltiae (NEMASHIELD® from BioWorks, Inc., USA;NEMASYS® from Becker Underwood Ltd., UK), S. kraussei L137 (NEMASYS® Lfrom Becker Underwood Ltd., UK), Streptomyces griseoviridis K61 (e.g.MYCOSTOP® from Verdera Oy, Espoo, Finland; Crop Protection 25, 468-475,2006), S. lydicus WYEC 108 (e.g. Actinovate® from Natural Industries,Inc., USA, U.S. Pat. No. 5,403,584), S. violaceusniger YCED-9 (e.g.DT-9® from Natural Industries, Inc., USA, U.S. Pat. No. 5,968,503),Talaromyces flavus V117b (e.g. PROTUS® from Prophyta, Germany),Trichoderma asperellum SKT-1 (e.g. ECO-HOPE® from Kumiai ChemicalIndustry Co., Ltd., Japan), T. asperellum ICC 012 (e.g. in TENET WP,REMDIER WP, BIOTEN WP from Isagro NC, USA, BIO-TAM from AgraQuest, USA),T. atroviride LC52 (e.g. SENTINEL® from Agrimm Technologies Ltd, NZ), T.atroviride CNCM 1-1237 (e.g. in Esquive WG from Agrauxine S.A., France,e.g. against pruning wound diseases on vine and plant root pathogens),T. fertile JM41R (NRRL 50759; e.g. RICHPLUS™ from Becker Underwood BioAg SA Ltd, South Africa), T. gamsii ICC 080 (e.g. in TENET WP, REMDIERWP, BIOTEN WP from Isagro N.C., USA, BIO-TAM from AgraQuest, USA), T.harzianum T-22 (e.g. PLANTSHIELD® der Firma BioWorks Inc., USA), T.harzianum TH 35 (e.g. ROOT PRO® from Mycontrol Ltd., Israel), T.harzianum T-39 (e.g. TRICHODEX® and TRICHODERMA 2000® from MycontrolLtd., Israel and Makhteshim Ltd., Israel), T. harzianum and T. viride(e.g. TRICHOPEL from Agrimm Technologies Ltd, NZ), T. harzianum ICC012and T. viride ICC080 (e.g. REMEDIER® WP from Isagro Ricerca, Italy), T.polysporum and T. harzianum (e.g. BINAB® from BINAB Bio-Innovation AB,Sweden), T. stromaticum (e.g. TRICOVAB® from C.E.P.L.A.C., Brazil), T.virens GL-21 (also named Gliocladium virens) (e.g. SOILGARD® from CertisLLC, USA), T. viride (e.g. TRIECO® from Ecosense Labs. (India) Pvt.Ltd., Indien, BIO-CURE® F from T. Stanes & Co. Ltd., Indien), T. virideTV1 (e.g. T. viride TV1 from Agribiotec srl, Italy) and Ulocladiumoudemansii HRU3 (e.g. in BOTRY-ZEN® from Botry-Zen Ltd, NZ).

Strains can be sourced from genetic resource and deposition centers:American Type Culture Collection, 10801 University Blvd., Manassas, Va.20110-2209, USA (strains with ATCC prefic); CABI Europe—InternationalMycological Institute, Bakeham Lane, Egham, Surrey, TW20 9TYNRRL, UK(strains with prefices CABI and IMI); Centraalbureau voorSchimmelcultures, Fungal Biodiversity Centre, Uppsalaan 8, PO Box 85167,3508 AD Utrecht, Netherlands (strains with prefic CBS); Division ofPlant Industry, CSIRO, Canberra, Australia (strains with prefix CC);Collection Nationale de Cultures de Microorganismes, Institut Pasteur,25 rue du Docteur Roux, F-75724 PARIS Cedex 15 (strains with prefixCNCM); Leibniz-lnstitut DSMZ-Deutsche Sammlung von Mikroorganismen undZellkulturen GmbH, Inhoffenstral3e 7 B, 38124 Braunschweig, Germany(strains with prefix DSM); International Depositary Authority of CanadaCollection, Canada (strains with prefix IDAC); Interntional Collectionof Micro-orgniasms from Plants, Landcare Research, Private Bag 92170,Auckland Mail Centre, Auckland 1142, New Zealand (strans with prefixICMP); IITA, PMB 5320, Ibadan, Nigeria (straisn with prefix IITA); TheNational Collections of Industrial and Marine Bacteria Ltd., TorryResearch Station, P.O. Box 31, 135 Abbey Road, Aberdeen, AB9 8DG,Scotland (strains with prefix NCIMB); ARS Culture Collection of theNational Center for Agricultural Utilization Research, AgriculturalResearch Service, U.S. Department of Agriculture, 1815 North UniversityStreet, Peoria, Ill. 61604, USA (strains with prefix NRRL); Departmentof Scientific and Industrial Research Culture Collection, AppliedBiochemistry Division, Palmerston North, New Zealand (strains withprefix NZP); FEPAGRO-Fundação Estadual de Pesquisa Agropecuária, RuaGonçalves Dias, 570, Bairro Menino Deus, Porto Alegre/RS, Brazil(strains with prefix SEMIA); SARDI, Adelaide, South Australia (strainswith prefix SRDI); U.S. Department of Agriculture, Agricultural ResearchService, Soybean and Alfalfa Research Laboratory, BARC-West, 10300Baltimore Boulevard, Building 011, Room 19-9, Beltsville, Md. 20705, USA(strains with prefix USDA: Beltsville Rhizobium Culture CollectionCatalog March 1987 USDA-ARS ARS-30:http://pdf.usaid.gov/pdf_docs/PNAAW891.pdf); and Murdoch University,Perth, Western Australia (strains with prefix WSM). Further strains maybe found at the Global catalogue of Microorganisms:http://gcm.wfcc.info/ andhttp://www.landcareresearch.co.nz/resources/collections/icmp and furtherreferences to strain collections and their prefixes athttp://refs.wdcm.org/collections.htm. Bacillus amyloliquefaciens subsp.plantarum MBI600 (NRRL B-50595) is deposited under accession number NRRLB-50595 with the strain designation Bacillus subtilis 1430 (andidentical to NCIMB 1237). Recently, MBI 600 has been re-classified asBacillus amyloliquefaciens subsp. plantarum based on polyphasic testingwhich combines classical microbiological methods relying on a mixture oftraditional tools (such as culture-based methods) and molecular tools(such as genotyping and fatty acids analysis). Thus, Bacillus subtilisMBI600 (or MBI 600 or MBI-600) is identical to Bacillusamyloliquefaciens subsp. plantarum MB1600, formerly Bacillus subtilisMB1600. Bacillus amyloliquefaciens MBI600 is known as plantgrowth-promoting rice seed treatment from Int. J. Microbiol. Res. 3(2)(2011), 120-130 and further described e.g. in US 2012/0149571 A1. Thisstrain MBI600 is e.g. commercially available as liquid formulationproduct INTEGRAL® (Becker-Underwood Inc., USA).

Bacillus subtilis strain FB17 was originally isolated from red beetroots in North America (System Appl. Microbiol 27 (2004) 372-379). ThisB. subtilis strain promotes plant health (US 2010/0260735 A1; WO2011/109395 A2). B. subtilis FB17 has also been deposited at ATCC undernumber PTA-11857 on Apr. 26, 2011. Bacillus subtilis strain FB17 may bereferred elsewhere to as UD1022 or UD10-22.

Bacillus amyloliquefaciens AP-136 (NRRL B-50614), B. amyloliquefaciensAP-188 (NRRL B-50615), B. amyloliquefaciens AP-218 (NRRL B-50618), B.amyloliquefaciens AP-219 (NRRL B-50619), B. amyloliquefaciens AP-295(NRRL B-50620), B. japonicum SEMIA 5079 (e.g. Gelfix 5 or Adhere 60 fromNitral Urbana Laoboratories, Brazil, a BASF Company), B. japonicum SEMIA5080 (e.g. GELFIX 5 or ADHERE 60 from Nitral Urbana Laoboratories,Brazil, a BASF Company), B. mojavensis AP-209 (NRRL B-50616), B.solisalsi AP-217 (NRRL B-50617), B. pumilus strain INR-7 (otherwisereferred to as BU-F22 (NRRL B-50153) and BU-F33 (NRRL B-50185)), B.simplex ABU 288 (NRRL B-50340) and B. amyloliquefaciens subsp. plantarumMBI600 (NRRL B-50595) have been mentioned i.a. in US patent appl.20120149571, U.S. Pat. No. 8,445,255, WO 2012/079073. Bradyrhizobiumjaponicum USDA 3 is known from U.S. Pat. No. 7,262,151.

Jasmonic acid or salts (jasmonates) or derivatives include withoutlimitation potassi-um jasmonate, sodium jasmonate, lithium jasmonate,ammonium jasmonate, dimethyl-ammonium jasmonate, isopropylammoniumjasmonate, diolammonium jasmonate, diethtriethanolammonium jasmonate,jasmonic acid methyl ester, jasmonic acid amide, jasmonic acidmethylamide, jasmonic acid-L-amino acid (amide-linked) conjugates (e.g.,conjugates with L-isoleucine, L-valine, L-leucine, or L-phenylalanine),12-oxo-phytodienoic acid, coronatine, coronafacoyl-L-serine,coronafacoyl-L-threonine, methyl esters of 1-oxo-indanoyl-isoleucine,methyl esters of 1-oxo-indanoyl-leucine, coronalon(2-[(6-ethyl-1-oxo-indane-4-carbonyl)-amino]-3-methyl-pentanoic acidmethyl ester), linoleic acid or derivatives thereof and cis-jasmone, orcombinations of any of the above.

Humates are humic and fulvic acids extracted from a form of lignite coaland clay, known as leonardite. Humic acids are organic acids that occurin humus and other organically derived materials such as peat andcertain soft coal. They have been shown to increase fertilizerefficiency in phosphate and micro-nutrient uptake by plants as well asaiding in the development of plant root systems.

The compounds of the invention may be mixed with soil, peat or otherrooting media for the protection of plants against seed-borne,soil-borne or foliar fungal diseases.

Examples of suitable synergists for use in the compositions includepiperonyl butoxide, sesamex, safroxan and dodecyl imidazole.

Suitable herbicides and plant-growth regulators for inclusion in thecompositions will depend upon the intended target and the effectrequired.

An example of a rice selective herbicide which may be included ispropanil. An example of a plant growth regulator for use in cotton isPIX™.

Some mixtures may comprise active ingredients which have significantlydifferent physical, chemical or biological properties such that they donot easily lend themselves to the same

The invertebrate pest (also referred to as “animal pest”), i.e. theinsects, arachnids and nematodes, the plant, soil or water in which theplant is growing or may grow can be contacted with the compounds of thepresent invention or composition(s) comprising them by any applicationmethod known in the art. As such, “contacting” includes both directcontact (applying the compounds/compositions directly on theinvertebrate pest or plant—typically to the foliage, stem or roots ofthe plant) and indirect contact (applying the compounds/compositions tothe locus of the invertebrate pest or plant).

-   -   The compounds of the present invention or the pesticidal        compositions comprising them may be used to protect growing        plants and crops from attack or infestation by animal pests,        especially insects, acaridae or arachnids by contacting the        plant/crop with a pesticidally effective amount of compounds of        the present invention. The term “crop” refers both to growing        and harvested crops.

The compounds of the present invention and the compositions comprisingthem are particularly important in the control of a multitude of insectson various cultivated plants, such as cereal, root crops, oil crops,vegetables, spices, ornamentals, for example seed of durum and otherwheat, barley, oats, rye, maize (fodder maize and sugar maize/sweet andfield corn), soybeans, oil crops, crucifers, cotton, sunflowers,bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet,eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks,pumpkin/squash, cabbage, iceberg lettuce, pepper, cucumbers, melons,Brassica species, melons, beans, peas, garlic, onions, carrots, tuberousplants such as potatoes, sugar cane, tobacco, grapes, petunias,geranium/pelargoniums, pansies and impatiens.

The compounds of the present invention are employed as such or in formof compositions by treating the insects or the plants, plant propagationmaterials, such as seeds, soil, surfaces, materials or rooms to beprotected from insecticidal attack with an insecticidally effectiveamount of the active compounds. The application can be carried out bothbefore and after the infection of the plants, plant propagationmaterials, such as seeds, soil, surfaces, materials or rooms by theinsects.

Moreover, invertebrate pests may be controlled by contacting the targetpest, its food supply, habitat, breeding ground or its locus with apesticidally effective amount of compounds of the present invention. Assuch, the application may be carried out before or after the infectionof the locus, growing crops, or harvested crops by the pest.

The compounds of the present invention can also be applied preventivelyto places at which occurrence of the pests is expected.

The compounds of the present invention may be also used to protectgrowing plants from attack or infestation by pests by contacting theplant with a pesticidally effective amount of compounds of the presentinvention. As such, “contacting” includes both direct contact (applyingthe compounds/compositions directly on the pest and/or plant—typicallyto the foliage, stem or roots of the plant) and indirect contact(applying the compounds/compositions to the locus of the pest and/orplant).

“Locus” means a habitat, breeding ground, plant, seed, soil, area,material or environment in which a pest or parasite is growing or maygrow.

In general, “pesticidally effective amount” means the amount of activeingredient needed to achieve an observable effect on growth, includingthe effects of necrosis, death, retardation, prevention, and removal,destruction, or otherwise diminishing the occurrence and activity of thetarget organism. The pesticidally effective amount can vary for thevarious compounds/compositions used in the invention. A pesticidallyeffective amount of the compositions will also vary according to theprevailing conditions such as desired pesticidal effect and duration,weather, target species, locus, mode of application, and the like.

In the case of soil treatment or of application to the pests dwellingplace or nest, the quantity of active ingredient ranges from 0.0001 to500 g per 100 m², preferably from 0.001 to 20 g per 100 m².

Customary application rates in the protection of materials are, forexample, from 0.01 g to 1000 g of active compound per m² treatedmaterial, desirably from 0.1 g to 50 g per m².

Insecticidal compositions for use in the impregnation of materialstypically contain from 0.001 to 95 weight %, preferably from 0.1 to 45weight %, and more preferably from 1 to 25 weight % of at least onerepellent and/or insecticide.

For use in treating crop plants, the rate of application of the activeingredients of this invention may be in the range of 0.1 g to 4000 g perhectare, desirably from 5 g to 500 g per hectare, more desirably from 5g to 200 g per hectare.

The compounds of the present invention are effective through bothcontact (via soil, glass, wall, bed net, carpet, plant parts or animalparts), and ingestion (bait, or plant part).

The compounds of the present invention may also be applied againstnon-crop insect pests, such as ants, termites, wasps, flies, mosquitos,crickets, or cockroaches.

For use against said non-crop pests, compounds of the present inventionare preferably used in a bait composition.

The bait can be a liquid, a solid or a semisolid preparation (e.g. agel). Solid baits can be formed into various shapes and forms suitableto the respective application e.g. granules, blocks, sticks, disks.Liquid baits can be filled into various devices to ensure properapplication, e.g. open containers, spray devices, droplet sources, orevaporation sources. Gels can be based on aqueous or oily matrices andcan be formulated to particular necessities in terms of stickyness,moisture retention or aging characteristics. The bait employed in thecomposition is a product, which is sufficiently attractive to inciteinsects such as ants, termites, wasps, flies, mosquitos, crickets etc.or cockroaches to eat it. The attractiveness can be manipulated by usingfeeding stimulants or sex pheromones. Food stimulants are chosen, forexample, but not exclusively, from animal and/or plant proteins (meat-,fish- or blood meal, insect parts, egg yolk), from fats and oils ofanimal and/or plant origin, or mono-, oligo- or polyorganosaccharides,especially from sucrose, lactose, fructose, dextrose, glucose, starch,pectin or even molasses or honey. Fresh or decaying parts of fruits,crops, plants, animals, insects or specific parts thereof can also serveas a feeding stimulant. Sex pheromones are known to be more insectspecific. Specific pheromones are described in the literature and areknown to those skilled in the art. For use in bait compositions, thetypical content of active ingredient is from 0.001 weight % to 15 weight%, desirably from 0.001 weight % to 5% weight % of active ingredient.

Formulations of compounds of the present invention as aerosols (e.g inspray cans), oil sprays or pump sprays are highly suitable for thenon-professional user for controlling pests such as flies, fleas, ticks,mosquitos or cockroaches. Aerosol recipes are preferably composed of theactive compound, solvents such as lower alcohols (e.g. methanol,ethanol, propanol, butanol), ketones (e.g. acetone, methyl ethylketone), paraffin hydrocarbons (e.g. kerosenes) having boiling ranges ofapproximately 50 to 250° C., dimethylformamide, N-methylpyrrolidone,dimethyl sulfoxide, aromatic hydrocarbons such as toluene, xylene,water, furthermore auxiliaries such as emulsifiers such as sorbitolmonooleate, oleyl ethoxylate having 3-7 mol of ethylene oxide, fattyalcohol ethoxylate, perfume oils such as ethereal oils, esters of mediumfatty acids with lower alcohols, aromatic carbonyl compounds, ifappropriate stabilizers such as sodium benzoate, amphoteric surfactants,lower epoxides, triethyl orthoformate and, if required, propellants suchas propane, butane, nitrogen, compressed air, dimethyl ether, carbondioxide, nitrous oxide, or mixtures of these gases.

The oil spray formulations differ from the aerosol recipes in that nopropellants are used.

For use in spray compositions, the content of active ingredient is from0.001 to 80 weights %, preferably from 0.01 to 50 weight % and mostpreferably from 0.01 to 15 weight %.

The compounds of the present invention and its respective compositionscan also be used in mosquito and fumigating coils, smoke cartridges,vaporizer plates or long-term vaporizers and also in moth papers, mothpads or other heat-independent vaporizer systems.

Methods to control infectious diseases transmitted by insects (e.g.malaria, dengue and yellow fever, lymphatic filariasis, andleishmaniasis) with compounds of the present invention and itsrespective compositions also comprise treating surfaces of huts andhouses, air spraying and impregnation of curtains, tents, clothingitems, bed nets, tsetse-fly trap or the like. Insecticidal compositionsfor application to fibers, fabric, knitgoods, nonwovens, nettingmaterial or foils and tarpaulins preferably comprise a mixture includingthe insecticide, optionally a repellent and at least one binder.Suitable repellents for example are N,N-Diethyl-meta-toluamide (DEET),N,N-diethylphenylacetamide (DEPA),1-(3-cyclohexan-1-yl-carbonyl)-2-methylpiperine,(2-hydroxymethylcyclohexyl) acetic acid lactone, 2-ethyl-1,3-hexandiol,indalone, Methylneodecanamide (MNDA), a pyrethroid not used for insectcontrol such as{(+/−)-3-allyl-2-methyl-4-oxocyclopent-2-(+)-enyl-(+)-trans-chrysantemate(Esbiothrin), a repellent derived from or identical with plant extractslike limonene, eugenol, (+)-Eucamalol (1), (−)-1-epi-eucamalol or crudeplant extracts from plants like Eucalyptus maculata, Vitex rotundifolia,Cymbopogan martinii, Cymbopogan citratus (lemon grass), Cymopogannartdus (citronella). Suitable binders are selected for example frompolymers and copolymers of vinyl esters of aliphatic acids (such as suchas vinyl acetate and vinyl versatate), acrylic and methacrylic esters ofalcohols, such as butyl acrylate, 2-ethylhexylacrylate, and methylacrylate, mono- and di-ethylenically unsaturated hydrocarbons, such asstyrene, and aliphatic diens, such as butadiene.

The impregnation of curtains and bednets is done in general by dippingthe textile material into emulsions or dispersions of the insecticide orspraying them onto the nets.

The compounds of the present invention and their compositions can beused for protecting wooden materials such as trees, board fences,sleepers, etc. and buildings such as houses, outhouses, factories, butalso construction materials, furniture, leathers, fibers, vinylarticles, electric wires and cables etc. from ants and/or termites, andfor controlling ants and termites from doing harm to crops or humanbeing (e.g. when the pests invade into houses and public facilities).The compounds of the present invention are applied not only to thesurrounding soil surface or into the under-floor soil in order toprotect wooden materials but it can also be applied to lumbered articlessuch as surfaces of the under-floor concrete, alcove posts, beams,plywoods, furniture, etc., wooden articles such as particle boards, halfboards, etc. and vinyl articles such as coated electric wires, vinylsheets, heat insulating material such as styrene foams, etc. In case ofapplication against ants doing harm to crops or human beings, the antcontroller of the present invention is applied to the crops or thesurrounding soil, or is directly applied to the nest of ants or thelike.

The compounds of the present invention are also suitable for thetreatment of plant propagation material, especially seeds, in order toprotect them from insect pest, in particular from soil-living insectpests and the resulting plant's roots and shoots against soil pests andfoliar insects.

The compounds of the present invention are particularly useful for theprotection of the seed from soil pests and the resulting plant's rootsand shoots against soil pests and foliar insects. The protection of theresulting plant's roots and shoots is preferred. More preferred is theprotection of resulting plant's shoots from piercing and suckinginsects, wherein the protection from aphids is most preferred.

The present invention therefore comprises a method for the protection ofseeds from insects, in particular from soil insects and of theseedlings' roots and shoots from insects, in particular from soil andfoliar insects, said method comprising contacting the seeds beforesowing and/or after pregermination with a compound of the presentinvention, including a salt thereof. Particularly preferred is a method,wherein the plant's roots and shoots are protected, more preferably amethod, wherein the plants shoots are protected form piercing andsucking insects, most preferably a method, wherein the plants shoots areprotected from aphids.

The term seed embraces seeds and plant propagules of all kinds includingbut not limited to true seeds, seed pieces, suckers, corms, bulbs,fruit, tubers, grains, cuttings, cut shoots and the like and means in apreferred embodiment true seeds.

The term seed treatment comprises all suitable seed treatment techniquesknown in the art, such as seed dressing, seed coating, seed dusting,seed soaking and seed pelleting.

The present invention also comprises seeds coated with or containing theactive compound.

The term “coated with and/or containing” generally signifies that theactive ingredient is for the most part on the surface of the propagationproduct at the time of application, although a greater or lesser part ofthe ingredient may penetrate into the propagation product, depending onthe method of application. When the said propagation product is(re)planted, it may absorb the active ingredient.

Suitable seed is seed of cereals, root crops, oil crops, vegetables,spices, ornamentals, for example seed of durum and other wheat, barley,oats, rye, maize (fodder maize and sugar maize/sweet and field corn),soybeans, oil crops, crucifers, cotton, sunflowers, bananas, rice,oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes,grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash,cabbage, iceberg lettuce, pepper, cucumbers, melons, Brassica species,melons, beans, peas, garlic, onions, carrots, tuberous plants such aspotatoes, sugar cane, tobacco, grapes, petunias, geranium/pelargoniums,pansies and impatiens.

In addition, the active compound may also be used for the treatmentseeds from plants, which tolerate the action of herbicides or fungicidesor insecticides owing to breeding, including genetic engineeringmethods.

For example, the active compound can be employed in treatment of seedsfrom plants, which are resistant to herbicides from the group consistingof the sulfonylureas, imidazolinones, glufosinate-ammonium orglyphosate-isopropylammonium and analogous active substances (see forexample, EP-A 242 236, EP-A 242 246) (WO 92/00377) (EP-A 257 993, U.S.Pat. No. 5,013,659) or in transgenic crop plants, for example cotton,with the capability of producing Bacillus thuringiensis toxins (Bttoxins) which make the plants resistant to certain pests (EP-A 142 924,EP-A 193 259), Furthermore, the active compound can be used also for thetreatment of seeds from plants, which have modified characteristics incomparison with existing plants consist, which can be generated forexample by traditional breeding methods and/or the generation ofmutants, or by recombinant procedures). For example, a number of caseshave been described of recombinant modifications of crop plants for thepurpose of modifying the starch synthesized in the plants (e.g. WO92/11376, WO 92/14827, WO 91/19806) or of transgenic crop plants havinga modified fatty acid composition (WO 91/13972).

The seed treatment application of the active compound is carried out byspraying or by dusting the seeds before sowing of the plants and beforeemergence of the plants.

Compositions which are especially useful for seed treatment are e.g.:

-   A Soluble concentrates (SL, LS)-   D Emulsions (EW, EO, ES)-   E Suspensions (SC, OD, FS)-   F Water-dispersible granules and water-soluble granules (WG, SG)-   G Water-dispersible powders and water-soluble powders (WP, SP, WS)-   H Gel-Formulations (GF)-   I Dustable powders (DP, DS)

Conventional seed treatment formulations include for example flowableconcentrates FS, solutions LS, powders for dry treatment DS, waterdispersible powders for slurry treatment WS, water-soluble powders SSand emulsion ES and EC and gel formulation GF. These formulations can beapplied to the seed diluted or undiluted. Application to the seeds iscarried out before sowing, either directly on the seeds or after havingpregerminated the latter.

In a preferred embodiment a FS formulation is used for seed treatment.Typically, a FS formulation may comprise 1-800 g/l of active ingredient,1-200 g/I Surfactant, 0 to 200 g/I antifreezing agent, 0 to 400 g/l ofbinder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent,preferably water.

Especially preferred FS formulations of compounds of the presentinvention for seed treatment usually comprise from 0.1 to 80% by weight(1 to 800 g/I) of the active ingredient, from 0.1 to 20% by weight (1 to200 g/I) of at least one surfactant, e.g. 0.05 to 5% by weight of awetter and from 0.5 to 15% by weight of a dispersing agent, up to 20% byweight, e.g. from 5 to 20% of an anti-freeze agent, from 0 to 15% byweight, e.g. 1 to 15% by weight of a pigment and/or a dye, from 0 to 40%by weight, e.g. 1 to 40% by weight of a binder (sticker/adhesion agent),optionally up to 5% by weight, e.g. from 0.1 to 5% by weight of athickener, optionally from 0.1 to 2% of an anti-foam agent, andoptionally a preservative such as a biocide, antioxidant or the like,e.g. in an amount from 0.01 to 1% by weight and a filler/vehicle up to100% by weight.

Seed Treatment formulations may additionally also comprise binders andoptionally colorants.

Binders can be added to improve the adhesion of the active materials onthe seeds after treatment. Suitable binders are homo- and copolymersfrom alkylene oxides like ethylene oxide or propylene oxide,polyvinylacetate, polyvinylalcohols, polyvinylpyrrolidones, andcopolymers thereof, ethylene-vinyl acetate copolymers, acrylic homo- andcopolymers, polyethyleneamines, polyethyleneamides andpolyethyleneimines, polysaccharides like celluloses, tylose and starch,polyolefin homo- and copolymers like olefin/maleic anhydride copolymers,polyurethanes, polyesters, polystyrene homo and copolymers.

Optionally, also colorants can be included in the formulation. Suitablecolorants or dyes for seed treatment formulations are Rhodamin B, C.I.Pigment Red 112, C.I. Solvent Red 1, pigment blue 15:4, pigment blue15:3, pigment blue 15:2, pigment blue 15:1, pigment blue 80, pigmentyellow 1, pigment yellow 13, pigment red 112, pigment red 48:2, pigmentred 48:1, pigment red 57:1, pigment red 53:1, pigment orange 43, pigmentorange 34, pigment orange 5, pigment green 36, pigment green 7, pigmentwhite 6, pigment brown 25, basic violet 10, basic violet 49, acid red51, acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10,basic red 108.

Examples of a gelling agent is carrageen (Satiagel®)

In the treatment of seed, the application rates of the compounds of thepresent invention are generally from 0.01 g to 10 kg per 100 kg of seed,preferably from 0.05 g to 5 kg per 100 kg of seed, more preferably from0.1 g to 1000 g per 100 kg of seed and in particular from 0.1 g to 200 gper 100 kg of seed.

The invention therefore also relates to seed comprising a compound ofthe present invention, including an agriculturally useful salt of it, asdefined herein. The amount of the compound of the present invention,including an agriculturally useful salt thereof will in general varyfrom 0.01 g to 10 kg per 100 kg of seed, preferably from 0.05 g to 5 kgper 100 kg of seed, in particular from 0.1 g to 1000 g per 100 kg ofseed. For specific crops such as lettuce the rate can be higher.

Methods which can be employed for treating the seed are, in principle,all suitable seed treatment and especially seed dressing techniquesknown in the art, such as seed coating (e.g. seed pelleting), seeddusting and seed imbibition (e.g. seed soaking). Here, “seed treatment”refers to all methods that bring seeds and the compounds of the presentinvention into contact with each other, and “seed dressing” to methodsof seed treatment which provide the seeds with an amount of thecompounds of the present invention, i.e. which generate a seedcomprising a compound of the present invention. In principle, thetreatment can be applied to the seed at any time from the harvest of theseed to the sowing of the seed. The seed can be treated immediatelybefore, or during, the planting of the seed, for example using the“planter's box” method. However, the treatment may also be carried outseveral weeks or months, for example up to 12 months, before plantingthe seed, for example in the form of a seed dressing treatment, withouta substantially reduced efficacy being observed.

Expediently, the treatment is applied to unsown seed. As used herein,the term “unsown seed” is meant to include seed at any period from theharvest of the seed to the sowing of the seed in the ground for thepurpose of germination and growth of the plant.

Specifically, a procedure is followed in the treatment in which the seedis mixed, in a suitable device, for example a mixing device for solid orsolid/liquid mixing partners, with the desired amount of seed treatmentformulations, either as such or after previous dilution with water,until the composition is distributed uniformly on the seed. Ifappropriate, this is followed by a drying step.

The compounds of the present invention, including their stereoisomers,veterinarily acceptable salts or N-oxides, are in particular alsosuitable for being used for combating parasites in and on animals.

An object of the present invention is therefore also to provide newmethods to control parasites in and on animals. Another object of theinvention is to provide safer pesticides for animals. Another object ofthe invention is further to provide pesticides for animals that may beused in lower doses than existing pesticides. And another object of theinvention is to provide pesticides for animals, which provide a longresidual control of the parasites.

The invention also relates to compositions comprising a parasiticidallyeffective amount of compounds of the present invention, including theirstereoisomers, veterinarily acceptable salts or N-oxides, and anacceptable carrier, for combating parasites in and on animals.

The present invention also provides a method for treating, controlling,preventing and protecting animals against infestation and infection byparasites, which comprises orally, topically or parenterallyadministering or applying to the animals a parasiticidally effectiveamount of a compound of the present invention, including itsstereoisomers, veterinarily acceptable salts or N-oxides, or acomposition comprising it.

The invention also provides the use of a compound of the presentinvention, including its stereoisomers, veterinarily acceptable salts orN-oxides, for treating or protecting an animal from infestation orinfection by invertebrate pests.

The invention also provides a process for the preparation of acomposition for treating, controlling, preventing or protecting animalsagainst infestation or infection by parasites which comprises aparasiticidally effective amount of a compound of the present invention,including its stereoisomers, veterinarily acceptable salts or N-oxides,or a composition comprising it.

Activity of compounds against agricultural pests does not suggest theirsuitability for control of endo- and ectoparasites in and on animalswhich requires, for example, low, non-emetic dosages in the case of oralapplication, metabolic compatibility with the animal, low toxicity, anda safe handling.

Surprisingly it has now been found that compounds of formula (I) andtheir stereoisomers, veterinarily acceptable salts, tautomers andN-oxides, are suitable for combating endo- and ectoparasites in and onanimals.

The compounds of the present invention, especially compounds of formula(I) and their stereoisomers, veterinarily acceptable salts, tautomersand N-oxides, and compositions comprising them are preferably used forcontrolling and preventing infestations of and infections in animalsincluding warm-blooded animals (including humans) and fish. They are forexample suitable for controlling and preventing infestations andinfections in mammals such as cattle, sheep, swine, camels, deer,horses, pigs, poultry, rabbits, goats, dogs and cats, water buffalo,donkeys, fallow deer and reindeer, and also in fur-bearing animals suchas mink, chinchilla and raccoon, birds such as hens, geese, turkeys andducks and fish such as fresh- and salt-water fish such as trout, carpand eels.

Compounds of the present invention, including their stereoisomers,veterinarily acceptable salts or N-oxides, and compositions comprisingthem are preferably used for controlling and preventing infestations andinfections in domestic animals, such as dogs or cats.

Infestations in warm-blooded animals and fish include, but are notlimited to, lice, biting lice, ticks, nasal bots, keds, biting flies,muscoid flies, flies, myiasitic fly larvae, chiggers, gnats, mosquitoesand fleas.

The compounds of the present invention, including their stereoisomers,veterinarily acceptable salts or N-oxides, and compositions comprisingthem are suitable for systemic and/or non-systemic control of ecto-and/or endoparasites. They are active against all or some stages ofdevelopment.

The compounds of the present invention are especially useful forcombating parasites of the following orders and species, respectively:

fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides canis,Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllusfasciatus, cockroaches (Blattaria—Blattodea), e.g. Blattella germanica,Blattella asahinae, Periplaneta americana, Periplaneta japonica,Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae,and Blatta orientalis,

flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes albopictus, Aedesvexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians,Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anophelesleucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphoravicina, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria,Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyiahominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pipiens,Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culisetainornata, Culiseta melanura, Dermatobia hominis, Fannia canicularis,Gasterophilus intestinalis, Glossina morsitans, Glossina palpalis,Glossina fuscipes, Glossina tachinoides, Haematobia irritans,Haplodiplosis equestris, Hippelates spp., Hypoderma lineata, Leptoconopstorrens, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoriapectoralis, Mansonia spp., Musca domestica, Muscina stabulans, Oestrusovis, Phlebotomus argentipes, Psorophora columbiae, Psorophora discolor,Prosimulium mixtum, Sarcophaga haemorrhoidalis, Sarcophaga sp., Simuliumvittatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanuslineola, and Tabanus similis,

lice (Phthiraptera), e.g. Pediculus humanus capitis, Pediculus humanuscorporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis,Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthusstramineus and Solenopotes capillatus.

ticks and parasitic mites (Parasitiformes): ticks (Ixodida), e.g. Ixodesscapularis, Ixodes holocyclus, Ixodes pacificus, Rhiphicephalussanguineus, Dermacentor andersoni, Dermacentor variabilis, Amblyommaamericanum, Ambryomma maculatum, Ornithodorus hermsi, Ornithodorusturicata and parasitic mites (Mesostigmata), e.g. Ornithonyssus bacotiand Dermanyssus gallinae,

Actinedida (Prostigmata) and Acaridida (Astigmata) e.g. Acarapis spp.,Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp.,Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp.,Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp.,Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp.,Notoedres spp., Knemidocoptes spp., Cytodites spp., and Laminosioptesspp.,

Bugs (Heteropterida): Cimex lectularius, Cimex hemipterus, Reduviussenilis, Triatoma spp., Rhodnius ssp., Panstrongylus ssp. and Ariluscritatus, Anoplurida, e.g. Haematopinus spp., Linognathus spp.,Pediculus spp., Phtirus spp., and Solenopotes spp,

Mallophagida (suborders Arnblycerina and Ischnocerina), e.g. Trimenoponspp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp.,Lepikentron spp., Trichodectes spp., and Felicola spp,

Roundworms Nematoda:

Wipeworms and Trichinosis (Trichosyringida), e.g. Trichinellidae(Trichinella spp.), (Trichuridae) Trichuris spp., Capillaria spp,

Rhabditida, e.g. Rhabditis spp, Strongyloides spp., Helicephalobus spp,

Strongylida, e.g. Strongylus spp., Ancylostoma spp., Necator americanus,Bunostomum spp. (Hookworm), Trichostrongylus spp., Haemonchuscontortus., Ostertagia spp., Cooperia spp., Nematodirus spp.,Dictyocaulus spp., Cyathostoma spp., Oesophagostomum spp., Stephanurusdentatus, Ollulanus spp., Chabertia spp., Stephanurus dentatus, Syngamustrachea, Ancylostoma spp., Uncinaria spp., Globocephalus spp., Necatorspp., Metastrongylus spp., Muellerius capillaris, Protostrongylus spp.,Angiostrongylus spp., Parelaphostrongylus spp. Aleurostrongylusabstrusus, and Dioctophyma renale,

Intestinal roundworms (Ascaridida), e.g. Ascaris lumbricoides, Ascarissuum, Ascaridia galli, Parascaris equorum, Enterobius vermicularis(Threadworm), Toxocara canis, Toxascaris leonine, Skrjabinema spp., andOxyuris equi,

Camallanida, e.g. Dracunculus medinensis (guinea worm)

Spirurida, e.g. Thelazia spp. Wuchereria spp., Brugia spp., Onchocercaspp., Dirofilari spp.a, Dipetalonema spp., Setaria spp., Elaeophoraspp., Spirocerca lupi, and Habronema spp.,

Thorny headed worms (Acanthocephala), e.g. Acanthocephalus spp.,Macracanthorhynchus hirudinaceus and Oncicola spp.,

Planarians (Plathelminthes):

Flukes (Trematoda), e.g. Faciola spp., Fascioloides magna, Paragonimusspp., Dicrocoelium spp., Fasciolopsis buski, Clonorchis sinensis,Schistosoma spp., Trichobilharzia spp., Alaria alata, Paragonimus spp.,and Nanocyetes spp.,

Cercomeromorpha, in particular Cestoda (Tapeworms), e.g.Diphyllobothrium spp., Tenia spp., Echinococcus spp., Dipylidiumcaninum, Multiceps spp., Hymenolepis spp., Mesocestoides spp.,Vampirolepis spp., Moniezia spp., Anoplocephala spp., Sirometra spp.,Anoplocephala spp., and Hymenolepis spp.

The present invention relates to the therapeutic and the non-therapeuticuse of compounds of the present invention and compositions comprisingthem for controlling and/or combating parasites in and/or on animals.The compounds of the present invention and compositions comprising themmay be used to protect the animals from attack or infestation byparasites by contacting them with a parasiticidally effective amount ofcompounds of the present invention and compositions containing them. Thecompounds of the present invention and compositions comprising them canbe effective through both contact (via soil, glass, wall, bed net,carpet, blankets or animal parts) and ingestion (e.g. baits). As such,“contacting” includes both direct contact (applying the pesticidalmixtures/compositions containing the compounds of the present inventiondirectly on the parasite, which may include an indirect contact at itslocus-P, and optionally also administrating the pesticidalmixtures/composition directly on the animal to be protected) andindirect contact (applying the compounds/compositions to the locus ofthe parasite). The contact of the parasite through application to itslocus is an example of a non-therapeutic use of compounds of the presentinvention. “Locus-P” as used above means the habitat, food supply,breeding ground, area, material or environment in which a parasite isgrowing or may grow outside of the animal.

In general, “parasiticidally effective amount” means the amount ofactive ingredient needed to achieve an observable effect on growth,including the effects of necrosis, death, retardation, prevention, andremoval, destruction, or otherwise diminishing the occurrence andactivity of the target organism. The parasiticidally effective amountcan vary for the various compounds/compositions of the presentinvention. A parasiticidally effective amount of the compositions willalso vary according to the prevailing conditions such as desiredparasiticidal effect and duration, target species, mode of application,and the like.

The compounds of the present invention can also be applied preventivelyto places at which occurrence of the pests or parasites are expected.

Administration can be carried out both prophylactically andtherapeutically.

Administration of the active compounds is carried out directly or in theform of suitable preparations, orally, topically/dermally orparenterally.

The compounds of the invention are better bio-degradable than those ofthe prior art and in addition retain a high level of pest control. Thismakes them superior in terms of environmental safety. In light of thestructural similarities of the compounds of formula I, this significantdifference in bio-degradability in favour of the compounds of theinvention is unexpected and cannot be derived from what is known fromthe prior art.

EXAMPLES

The present invention is now illustrated in further details by thefollowing examples, without imposing any limitation thereto.

I. Preparation Examples

Compounds can be characterized e.g. by coupled High Performance LiquidChromatography/mass spectrometry (HPLC/MS), by ¹H-NMR and/or by theirmelting points.

Analytical HPLC column:

Method A: Analytical UPLC column: Phenomenex Kinetex 1.7 μm XB-C18 100A;50×2.1 mm from Phenomenex, Germany. Elution: acetonitrile+0.1%trifluoroacetic acid (TFA)/water+0.1% trifluoroacetic acid (TFA) in aratio from 5:95 to 100:0 in 1.5 min at 60° C. Flow: 0.8 mL/min to 1mL/min in 1.5 min. MS-method: ESI positive.

¹H-N M R: The signals are characterized by chemical shift (ppm, δ[delta]) vs. tetramethylsilane, respectively CDCl₃ for ¹³C-NMR, by theirmultiplicity and by their integral (relative number of hydrogen atomsgiven). The following abbreviations are used to characterize themultiplicity of the signals: m=multiplet, q=quartet, t=triplet,d=doublet and s=singlet.

Abbreviations used are: d for day(s), h for hour(s), min for minute(s),r.t./room temperature for 20-25° C., THF for tetrahydrofuran, DCE fordichloroethane, PyBroP for bromotripyrrolidinophosphoniumhexafluorophosphate.

C.1 Compound Examples 1

Compound examples 1-1 to 1-138 correspond to compounds of formula C.1:

wherein R^(2a), R^(2b), R^(2c) and Y of each synthesized compound isdefined in one row of table C.1 below.

The compounds were synthesized in analogy to Synthesis Example S.1.

TABLE C.1 HPLC-MS: Method, R_(t) (min) & [M + H]⁺ Ex. R^(2a), R^(2b),R^(2c) —Y or ¹H-NMR 1-1 Cl, F, Cl —OCH₃ A 1.559 477.5 1-2 Cl, F, Cl —OHA 1.446 461.4 1-3 Cl, F, Cl —NHCH₂-cyclopropyl ¹H NMR (400 MHz, CDCl₃):δ 7.6 (m, 2H), 7.5 (m, 1H), 7.2 (m, 1H), 6.0 (s, 1H), 4.2 (d, 1H), 3.8(d, 1H), 3.4-3.3 (m, 2H), 3.3-3.1 (m, 4H), 2.2-2.1 (m, 2H), 1.1-1.0 (m,1H), 0.6-0.5 (m, 2H), 0.3-0.2 (m, 2H). 1-4 Cl, F, Cl —NHCH₂C(═O)NHCH₂CF₃A 1.355 599.8 1-5 Cl, F, Cl —NH-(1,1-dioxo-thietan-3-yl) A 1.402 564.31-6 Cl, F, Cl —NHCH₂-(2-pyridyl) A 1.248 551.4 1-7 Cl, F, Cl—NHCH₂-(2-pyrimidinyl) A 1.432 552.4 1-8 Cl, F, Cl —NHCH₂-(thietan-3-yl)A 1.464 546.8 1-9 Cl, F, Cl —NH-(thietan-3-yl) A 1.460 532.8 1-10 Cl, F,Cl —NH-(1-oxo-thietan-3-yl) A 1.305 548.8 1-11 Cl, F, Cl —NHCH₂CH═CH₂ A1.440 500.8 1-12 Cl, F, Cl —NHCH₂CF₃ A 1.467 542.8 1-13 Cl, F, Cl—NH-(1-cyano-cyclopropyl) A 1.410 525.9 1-14 Cl, F, Cl —NHCH₂C≡CH A1.409 498.8 1-15 Cl, F, Cl —NH₂ A 1.460 460.4 1-16 Cl, F, Cl—NHNH-(2-pyrimidinyl) A 1.446 553.4 1-17 Cl, F, Cl —NHCH₂CN A 1.515499.4 1-18 Cl, F, Cl —NH—CH₂-(1,1-dioxo-thietan- A 1.342 578.9 3-yl)1-19 Cl, F, Cl —NH-(2,2-dimethyl-1,1-dioxo- A 1.430 592.9 thietan-3-yl)1-20 Cl, F, Cl —NH-(2,2-dimethylthietan-3-yl) A 1.538 561.3 1-21 Cl, F,Cl —NHCH₂-(1,1-dioxothietan-2-yl) A 1.372 579.3 1-22 Cl, F, Cl—NHCH₂—CH═CH—CH₃ (trans) A 1.479 514.9 1-23 Cl, F, Cl —NHCH═NOCH₃ A1.513 518.0 1-24 Cl, H, Cl —NH₂ A 1.319 442.9 1-25 Cl, H, Cl—NHNH-(2-pyrimidinyl) A 1.317 535.9 1-26 Cl, H, Cl —NHCH═NOCH₃ A 1.488500.0 1-27 Cl, H, Cl —NHCH₂-(2-pyridyl) A 1.259 534.0 1-28 Cl, H, Cl—NHCH₂C(═O)NHCH₂CF₃ A 1.369 582.0 1-29 Cl, H, Cl —NHCH₂CF₃ A 1.463 524.91-30 Cl, H, Cl —NHCH₂-(2-pyrimidinyl) A 1.357 535.0 1-31 Cl, H, Cl—NH-cyclopropyl A 1.404 483.0 1-32 Cl, H, Cl —NHCH₂-(thiazol-4-yl) A1.380 539.9 1-33 Cl, H, Cl —NH-(1,1-dioxo-thietan-3-yl) A 1.347 547.01-34 Cl, H, Cl —NH-(thietan-3-yl) A 1.450 514.9 1-35 Cl, H, Cl—NHCH₂-cyclopropyl A 1.456 496.9 1-36 Cl, H, Cl—NHCH₂-(1,1-dioxo-thietan-3- A 1.353 561.0 yl) 1-37 Cl, H, Cl—NH—CH(CH₃)—C(═O)NHCH₂CF₃ A 1.403 596.0 1-38 Cl, H, Cl—NH-[(4R)-2-ethyl-3-oxo- A 1.377 556.0 isoxazolidin-4-yl] 1-39 Cl, H, Cl—NH-[(4R)-3-oxo-2-(2,2,2- A 1.425 609.9trifluoroethyl)isoxazolidin-4-yl] 1-40 Cl, H, Cl —N(CH₃)—CH₂-(2-pyridyl)A 1.284 548.5 1-41 Cl, H, Cl —N(CH₂CH₃)—CH₂-(2-pyridyl) A 1.313 562.11-42 Cl, H, Cl —NH-(1-oxo-thietan-3-yl) A 1.304 531.0 1-43 Cl, H, Cl—NH-[(4S)-2-ethyl-3-oxo- A 1.396 556.0 isoxazolidin-4-yl] 1-44 Cl, F, Cl—NH—CH₂CH₃ A 1.428 489.0 1-45 Cl, F, Cl —NHCH₂C(═O)NHCH₂CH₃ A 1.350548.0 1-46 Cl, F, Cl —NH-cyclopropyl A 1.430 503.0 1-47 Cl, F, Cl—NHCH₂C(═O)NH-cyclopropyl A 1.358 558.0 1-48 Cl, F, Cl—NHCH₂C(═O)NHCH₂CH₂F A 1.334 564.0 1-49 Cl, F, Cl —NHCH₂C(═O)NHCH₂CHF₂ A1.359 582.0 1-50 Cl, F, Cl —NHCH₂-(2,2- A 1.466 551.0difluorocyclopropyl) 1-51 Cl, F, Cl —NHCH₂C(═O)NHCH₂C≡CH A 1.347 556.01-52 Cl, F, Cl —NHCH₂C(═O)—NHCH₂CH═CH₂ A 1.368 558.0 1-53 Cl, F, Cl—NHCH₂C(═O)—NHCH₃ A 1.315 532.0 1-54 Cl, F, Cl —NHCH₂-(4-thiazolyl) A1.402 558.0 1-55 Cl, F, Cl —NH-(3-tetrahydrofuranyl) A 1.395 531.0 1-56Cl, H, Cl —OH ¹H NMR (400 MHz, CDCl₃): δ 7.96 (d, 1H), 7.51 (s, 2H),7.43 (s, 1H), 7.26 (d, 1H), 4.15 (d, 1H), 3.76 (d, 1H), 3.40-3.33 (m,2H), 3.24-3.20 (m, 2H), 2.20-2.10 (m, 2H) 1-57 Cl, H, Cl—NHCH₂-(thietan-3-yl) A 1.446 529.0 1-58 Cl, F, Cl —NHCH₂-cyclobutyl A1.524 529.1 1-59 Cl, F, Cl —NH-(3,3-difluorocyclobutyl) A 1.471 551.01-60 Cl, F, Cl —NHCH₂-(3,3- A 1.477 565.0 difluorocyclobutyl) 1-61 Cl,F, Cl —NH-[(4R)-3-oxo-2-(2,2,2- A 1.426 627.9trifluoroethyl)isoxazolidin-4-yl] 1-62 Cl, F, Cl—NH-[(4S)-2-ethyl-3-oxo- A 1.385 574.0 isoxazolidin-4-yl] 1-63 Cl, F, Cl—NHCH₂-(3-pyridazinyl) A 1.303 552.9 1-64 Cl, F, Cl—NHCH₂-(5-bromopyrimidin-2-yl) A 1.454 632.8 1-65 Cl, F, Cl —NHCH₂-[(1-A 1.464 564.9 difluoromethyl)cyclopropyl] 1-66 Cl, F, Cl—NHCH₂C(═O)—NHCH₂- A 1.394 572.0 cyclopropyl 1-67 Cl, F, Cl—NH-cyclobutyl A 1.466 514.9 1-68 Cl, F, Cl —NHCH₂-[4,6-bis(trifluoro- A1.546 689.0 methyl)pyrimidin-2-yl] 1-69 Cl, F, Cl —NHCH₂-(2,2- A 1.526584.9 dichlorocyclopropyl) 1-70 Cl, F, Cl —NHCH₂CCl═CCl₂ A 1.560 604.91-71 Cl, F, Cl —NHCH₂-[4-(trifluoro- A 1.480 621.0methyl)pyrimidin-2-yl] 1-72 Cl, F, Cl —NHCH₂-(5-chloropyrimidin-2-yl) A1.463 588.9 1-73 Cl, F, Cl —NHCH₂-(4-methyl-pyrimidin-2-yl) A 1.396566.9 1-74 Cl, F, Cl —NHCH₂-(4,6-dimethyl- A 1.411 581.0 pyrimidin-2-yl)1-75 Cl, F, Cl —NHCH₂-[4-methyl-6- A 1.496 635.0(trifluoromethyl)pyrimidin-2-yl 1-76 Cl, F, H —NHCH₂-(2-pyrimidinyl) A1.290 519.0 1-77 Cl, F, H —NHCH₂-(2-pyridyl) A 1.148 518.1 1-78 Cl, F, H—NHCH₂C(═O)NHCH₂CF₃ A 1.300 566.0 1-79 Cl, F, H—NH-(1,1-dioxo-thietan-3-yl) A 1.281 531.0 1-80 Cl, F, Cl —H A 1.525445.9 1-81 Cl, F, H —OH A 1.346 428.0 1-82 Cl, F, Cl—NHCH₂-(2-methyl-tetrazol-5-yl) A 1.373 557.0 1-83 Cl, F, Cl—NHCH₂-(5-fluoro-pyrimidin-2-yl) A 1.418 571.0 1-84 Cl, F, Cl—NH-(3-pyridyl) A 1.241 538.0 1-85 Cl, F, Cl —NHNHC(═O)NHCH₂CF₃ A 1.338600.9 1-86 Cl, F, Cl —NHCH₂-(1,2,4-oxadiazol-3-yl) A 1.375 542.9 1-87Cl, F, Cl —NHCH₂-(1,3,4-thiadiazol-2-yl) A 1.363 558.9 1-88 Cl, F, Cl—NHCH₂-(4-chloro-pyrimidin- A 1.440 588.8 2-yl) 1-89 Cl, F, Cl—NHCH₂-(5-methyl-pyrimidin- A 1.404 567.0 2-yl) 1-90 Cl, F, Cl—NH-[(4R)-2-ethyl-3-oxo- A 1.393 574.1 isoxazolidin-4-yl] 1-91 Cl, F, Cl—NHCH₂CH₂SO₂CH₃ A 1.336 567.0 1-92 Cl, F, Cl —NHCH₂-(1-methyl-1,2,3- A1.332 556.0 triazol-4-yl) 1-93 Cl, F, Cl —NHCH₂-(1-methyl-1,2,4- A 1.307556.0 triazol-3-yl) 1-94 Cl, F, Cl 3-ethyl-4-oxo-imidazolidin-1-yl A1.375 558.0 1-95 Cl, F, Cl 4-oxo-3-(2,2,2- A 1.426 612.0trifluoroethyl)imidazolidin-1-yl 1-96 Cl, F, Cl—NHCH₂-(1-methyl-tetrazol-5-yl) A 1.351 557.0 1-97 Cl, F, Cl—NHNHC(═O)NHCH₂CF₂H ¹H NMR (400 MHz, d₆-DMSO): δ 10.0 (s, 1H), 8.2 (s,1H), 7.8 (m, 2H), 7.6 (d, 1H), 7.5 (d, 1H), 6.8 (s, 1H), 6.2-5.8 (m,1H), 4.5-4.3 (m, 2H), 3.6-3.4 (m, 2H), 3.2-3.0 (m, 4H), 2.1-1.9 (m, 2H)1-98 Cl, F, Cl —NHNHC(═O)NHCH₂CH₃ A 1.309 547.0 1-99 Cl, F, Cl—NH-(5-pyrimidinyl) A 1.404 539.0 1-100 Cl, F, Cl —NHNHC(═O)NHCH₃ A1.275 533.0 1-101 Cl, F, Cl —NHCH₂-(oxazol-2-yl) A 1.387 554.1 1-102 Cl,F, Cl —NHN(CH₃)-(2-pyrimidinyl) A 1.407 568.1 1-103 Cl, F, Cl—NHCH₂CH₂SCH₃ A 1.466 535.0 1-104 Cl, F, Cl —NH-[2-oxo-1-(2,2,2- A 1.413626.1 trifluoroethyl)pyrrolidin-3-yl] 1-105 Cl, F, Cl —NH-(2-pyrazinyl)A 1.467 539.0 1-106 Cl, F, Cl —NH-(1-methyl-pyrazol-3-yl) A 1.422 541.11-107 Cl, F, Cl —NHCH₂-(1- A 1.525 583.1 (trifluoromethyl)cyclopropyl)1-108 Cl, F, Cl —NH-(3-methyl-isothiazol-5-yl) A 1.460 558.0 1-109 Cl,F, Cl —NHNH-(2-pyridyl) A 1.164 553.0 1-110 Cl, F, Cl—NH-(3-pyridazinyl) A 1.419 539.0 1-111 Cl, F, Cl—NHCH₂-(1,3-dioxolan-2-yl) A 1.399 547.1 1-112 Cl, F, Cl—NH-(1-methyl-2-oxo- A 1.336 558.0 pyrrolidin-3-yl) 1-113 Cl, F, Cl—NHCH₂-(4-pyrimidinyl) A 1.355 553.1 1-114 Cl, F, Cl—NHCH₂-(1-methyl-pyrazol-3-yl) A 1.376 555.1 1-115 Cl, F, Cl—NHCH₂CH₂CF₂H A 1.444 539.1 1-116 Cl, F, Cl—NHCH₂CH₂-(1,3-dioxolan-2-yl) A 1.421 561.1 1-117 Cl, F, Cl—NH-(1-ethyl-2-oxo-pyrrolidin- A 1.369 572.1 3-yl) 1-118 Cl, F, Cl—NHCH₂-(4-oxazolyl) A 1.374 542.0 1-119 Cl, F, Cl—NHCH₂-(4-methyl-1,2,4- A 1.207 556.1 triazol-3-yl) 1-120 Cl, F, Cl—NHCH₂-(3-isoxazolyl) A 1.403 542.1 1-121 Cl, F, Cl—NHCH₂-(2-methyl-pyrazol-3-yl) A 1.369 555.1 1-122 Cl, F, Cl—NH-(1-methyl-5-oxo-1,2,4- A 1.324 558.1 triazol-4-yl) 1-123 F, H, OCF₃—NHCH₂-(2-pyrimidinyl) A 1.342 569.1 1-124 F, H, OCF₃ —NHCH₂-(2-pyridyl)A 1.177 568.1 1-125 Cl, F, Cl —NH-[(4R)-2-methyl-3-oxo- A 1.358 560.1isoxazolidin-4-yl] 1-126 Cl, F, Cl —NHCH₂-cyclopentyl A 1.558 543.01-127 Cl, F, Cl —NHCH₂-(2-tetrahydrofuranyl) A 1.439 545.1 1-128 Cl, F,Cl —NHCH₂CF₂H A 1.438 524.9 1-129 Cl, F, Cl —NHCH₂CFH₂ A 1.406 507.11-130 Cl, F, Cl —NHCH₂-(1-cyano- A 1.412 540.1 cyclopropyl) 1-131 Cl, F,Cl —NH-(2,2-difluorocyclopropyl) A 1.450 537.0 1-132 Cl, F, Cl—NHCH₂-(1-oxo-thietan-3-yl) A 1.302 563.1 1-133 Cl, F, Cl—NH-(4-pyridazinyl) A 1.277 539.0 1-134 F, H, OCF₃—NH-(1,1-dioxo-thietan-3-yl) A 1.330 581.0 1-135 F, H, OCF₃—NHCH₂C(═O)NHCH₂CF₃ A 1.356 616.1 1-136 Cl, F, Cl —N═S(CH₂CH₃)₂ A 1.349549.0 1-137 Cl, F, Cl —NH-(1-cyano-cyclobutyll) A 1.454 540.1 1-138 F,H, OCF₃ —NH-[(4R)-2-ethyl-3-oxo- A 1.363 590.1 isoxazolidin-4-yl]

Synthesis Example S.1 N-(Cyclopropylmethyl)-7-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]indane-4-carboxamide

(Compound example 1-3; compound of formula C.1, wherein R^(2a) andR^(2c) are Cl, R^(2b) is F, and —Y is —NHCH₂-cyclopropyl)

(7-Acetylindan-4-yl) trifluoromethanesulfonate (CAS 1312609-69-0) wassynthesized as described in US 2011/0152246 (p. 118, compound I-IIIf).

Step 1: Methyl 7-acetylindane-4-carboxylate

To a solution of (7-acetylindan-4-yl) trifluoromethanesulfonate (40 g)in methanol (357 mL) were added Na₂CO₃ (27.5 g) and[1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(11) (Pd(dppf)Cl₂,9.5 g). The solution was pressurized with carbon monoxide (50 Psi) andheated at 50° C. for 5 h. Then, the mixture was filtered and thefiltrate was concentrated. The residue was dissolved in CH₂Cl₂ andwashed with brine, dried (Na₂SO₄), filtered and concentrated to give aresidue, which was purified by flash chromatography on silica gel(petroleum ether/ethyl acetate) to afford the product (18.3 g, 64%).

¹H NMR (400 MHz, CDCl₃): δ 7.9 (d, 1H), 7.7 (d, 1H), 4.0 (s, 3H),3.3-3.2 (m, 4H), 2.6 (s, 3H), 2.1 (m, 2H).

Step 2: Methyl7-[(3-(3,5-dichloro-4-fluoro-phenyl)-4,4,4-trifluoro-but-2-enoyl]indane-4-carboxylate

To a solution of the product of step 1 (12 g) and1-(3,5-dichloro-4-fluoro-phenyl)-2,2,2-trifluoro-ethanone (28.7 g, CAS1190865-44-1) in DCE (100 mL) was added K₂CO₃ (7.6 g) and triethylamine(7.6 mL). The reaction was stirred at reflux overnight. Then, themixture was cooled to r.t., filtered and concentrated to give a residue,which was purified by flash chromatography on silica gel (petroleumether/ethyl acetate) to afford the product (18.75 g, 74%).

¹H NMR (400 MHz, CDCl₃): δ 7.8 (m, 1H), 7.5 (m, 1H), 7.3 (m, 1H), 7.2(m, 2H), 3.9 (s, 3H), 3.2 (m, 2H), 3.1 (m, 2H), 2.0 (m, 2H).

Step 3: Methyl7-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]indane-4-carboxylate(Compound Example 1-1)

To a solution of the product of step 2 (10 g) in THF (167 mL) was addedhydroxylamine hydrochloride (3 g), followed by a drop wise addition of asolution of NaOH (3.5 g) in water (83 mL). The reaction was stirred atr.t. overnight, and concentrated. The residue was taken up in ethylacetate, and the organic layer was washed with water (3×), dried(Na₂SO₄), filtered and concentrated to give a residue, which waspurified by flash chromatography on silica gel (petroleum ether/ethylacetate) to afford the product (6 g, 58%).

¹H NMR (400 MHz, MeOH-d₄): δ 7.9 (d, 1H), 7.8 (m, 2H), 7.4 (d, 1H), 4.3(d, 1H), 4.1 (d, 1H), 3.9 (s, 3H), 3.3 (m, 2H), 3.2 (m, 2H), 2.1 (m,2H).

Step 5:7-[5-(3,5-Dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]indane-4-carboxylicacid (Compound Example 1-2)

At 0° C., the product of step 4 (4.5 g) in THF (45 mL) was treated witha solution of LiOH (0.45 g) in water (5 mL), and the mixture stirred atr.t. for 5 h. Then, more LiOH (0.2 g) was added, and the reaction wasstirred at r.t. overnight. Subsequently, 10% aqueous HCl was added toadjust the pH of the reaction to pH 3-4. The organic layer was dilutedwith CH₂C₁₂, washed with water (2×), dried (Na₂SO₄), filtered, andconcentrated. The obtained residue was purified by trituration (hexanes)to afford the product (3.35 g, 77%).

¹H NMR (400 MHz, d₆-DMSO): δ 13.0 (s, 1H), 7.9-7.8 (m, 3H), 7.6-7.5 (m,1H), 4.4-4.3 (m, 2H), 3.3-3.2 (m, 2H), 3.2-3.0 (m, 2H), 2.1-1.9 (m, 2H).

Step 6:N-(Cyclopropylmethyl)-7-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]indane-4-carboxamide(Compound Example 1-3)

To a solution of the product of step 5 (0.23 g), cyclopropylmethylamine(0.04 g) and PyBroP (0.28 g) in CH₂Cl₂ (15 mL) at r.t. was addedN,N-diisopropylethylamine (0.26 g). The reaction was stirred at r.t.overnight. Then, the reaction was diluted with CH₂Cl₂, washed with water(2×), dried (Na₂SO₄), filtered and concentrated to give a residue, whichwas purified by flash chromatography on silica gel to afford the product(0.21 g, 82%).

¹H NMR (400 MHz, CDCl₃): δ 7.6 (m, 2H), 7.5 (m, 1H), 7.2 (m, 1H), 6.0(s, 1H), 4.2 (d, 1H), 3.8 (d, 1H), 3.4-3.3 (m, 2H), 3.3-3.1 (m, 4H),2.2-2.1 (m, 2H), 1.1-1.0 (m, 1H), 0.6-0.5 (m, 2H), 0.3-0.2 (m, 2H).

C.2 Compound Examples 2

Compound examples 2-1 to 2-24 correspond to compounds of formula C.2:

wherein R^(2a), R^(2b), R^(2c) and Y of each synthesized compound isdefined in one row of table C.2 below.

The compounds were synthesized in analogy to Synthesis Example S.2.

TABLE C.2 HPLC-MS: Method, R_(t) (min) & [M + H]⁺ Ex. R^(2a), R^(2b),R^(2c) —Y or ¹H-NMR 2-1 Cl, F, Cl —OH A 1.500 459.4 2-2 Cl, F, Cl —OCH₃A 1.661 473.4 2-3 Cl, F, Cl —NH-(1,1-dioxo-thietan-3-yl) ¹H NMR (400MHz, CDCl₃): δ 7.5 (m, 2H), 7.35 (m, 2H), 7.2 (m, 1H), 6.7 (d, 1H),5.0-4.85 (m, 2H), 4.7-4.6 (m, 2H), 4.45 (d, 1H), 4.1-4.0 (m, 2H), 3.8(d, 1H), 3.4 (d, 1H), 3.3-3.1 (m, 4H), 2.2-2.1 (m, 2H). 2-4 Cl, F, Cl—NH-(thietan-3-yl) A 1.526 532.2 2-5 Cl, F, Cl —NHCH₂-(thietan-3-yl) A1.527 544.8 2-6 Cl, F, Cl —NHCH₂-cyclopropyl A 1.393 514.6 2-7 Cl, F, Cl—NHCH₂C(═O)NHCH₂CF₃ A 1.311 599.6 2-8 Cl, F, Cl —NH-(1-oxo-thietan-3-yl)A 1.395 546.7 2-9 Cl, F, Cl —NHCH₂-(2-pyridyl) A 1.125 549.9 2-10 Cl, F,Cl —NHCH₂-(2-pyrimidinyl) A 1.284 550.9 2-11 Cl, F, Cl—NH—CH₂-(1,1-dioxo-thietan- A 1.265 576.9 3-yl) 2-12 Cl, H, Cl—NHNH-(2-pyrimidinyl) A 1.241 534.0 2-13 Cl, H, Cl —NHCH₂-(2-pyridyl) A1.158 532.0 2-14 Cl, H, Cl —NHCH₂C(═O)NHCH₂CF₃ A 1.302 580.0 2-15 Cl, H,Cl —OH A 1.351 441.9 2-16 Cl, H, Cl —OCH₃ A 1.529 455.9 2-17 Cl, H, Cl—NHCH₂-(2-pyrimidinyl) A 1.291 533.0 2-18 Cl, H, Cl —NH-cyclopropyl A1.347 481.0 2-19 Cl, H, Cl —NH-(1,1-dioxo-thietan-3-yl) A 1.289 545.02-20 Cl, H, Cl —NHCH₂-(4-thiazol) A 1.319 538.0 2-21 Cl, H, Cl—NH-[(4R)-2-ethyl-3-oxo- A 1.325 554.0 isoxazolidin-4-yl] 2-22 Cl, H, Cl—NHCH(CH₃)—C(═O)NHCH₂CF₃ A 1.357 594.0 2-23 Cl, H, Cl —NH-(thietan-3-yl)A 1.404 513.0 2-24 Cl, H, Cl —NH-(1-oxo-thietan-3-yl) A 1.232 529.0

Synthesis Example S.27-[3-(3,5-Dichloro-4-fluoro-phenyl)-3-(trifluoromethyl)-2,4-dihydropyrrol-5-yl]-N-(1,1-dioxothietan-3-yl)indane-4-carboxamide

(Compound example 2-3; compound of formula C.2, wherein R^(2a) andR^(2c) are Cl, R^(2b) is F and —Y is —NH-(1,1,-dioxo-thietan-3-yl))

Step 1: Methyl7-[3-(3,5-dichloro-4-fluoro-phenyl)-4,4,4-trifluoro-3-(nitromethyl)butanoyl]indane-4-carboxylate

To a solution of methyl7-[(3-(3,5-dichloro-4-fluoro-phenyl)-4,4,4-trifluoro-but-2-enoyl]indane-4-carboxylate(i.e. the product of Synthesis Example S.1, step 2, 10 g) in CH₃CN (400mL) was added 1,8-diazabicyclo[5.4.0] undec-7-ene (“DBU”, 16.6 g) andCH₃NO₂ (6 g) at r.t. The mixture was stirred for 20 min, and thenadjusted to pH 6 with aqueous 1 M HCl solution. The aqueous phase wasextracted with ethyl acetate (3×150 mL). The organic layers werecombined, concentrated and the obtained residue was purified by flashchromatography on silica gel (petroleum ether/ethyl acetate) to affordthe product (6 g, 52%).

¹H NMR (400 MHz, CDCl₃): δ 7.89 (d, 1H), 7.66 (d, 1H), 7.21-7.19 (m,2H), 5.52 (d, 1H), 5.39 (d, 1H), 4.04 (d, 1H), 3.91-3.87 (m, 4H),3.25-3.15 (m, 2H), 3.06-2.99 (m, 2H), 2.1-1.9 (m, 2H).

Step 2: Methyl7-[3-(3,5-dichloro-4-fluoro-phenyl)-3-(trifluoromethyl)-2,4-dihydropyrrol-5-yl]indane-4-carboxylate(Compound 2-2)

To a solution of the product of step 2 (6 g) in CH₃OH (100 mL) was addedacetic acid (100 mL) and iron powder (1.9 g). The mixture was stirred at70° C. overnight, and then concentrated. Water (20 mL) was added and theaqueous layer was extracted with ethyl acetate (3×100 mL). The combinedorganic layers were concentrated and the obtained residue was purifiedby flash chromatography on silica gel (petroleum ether/ethyl acetate) toafford the product (3.1 g, 56%).

¹H NMR (400 MHz, CDCl₃): δ 7.90 (d, 1H), 7.47 (d, 1H), 7.35-7.30 (m,2H), 4.94 (d, 1H), 4.47 (d, 1H), 3.93 (s, 3H), 3.81 (d, 1H), 3.49 (d,1H), 3.35-3.25 (m, 2H), 3.25-3.20 (m, 2H), 2.15-1.06 (m, 2H).

Step 3:7-[3-(3,5-Dichloro-4-fluoro-phenyl)-3-(trifluoromethyl)-2,4-dihydropyrrol-5-yl]indane-4-carboxylicacid (Compound 2-1)

At 0° C., the product of step 2 (1.66 g) in THF (25 mL) was treated witha solution of LiOH (0.17 g) in water (10 mL), and the mixture stirred atr.t. overnight. Then, more LiOH (0.1 g) was added, and the reaction wasstirred at 30° C. for 4 h. 10% aqueous HCl was added to adjust the pH ofthe reaction to pH 3-4. More water was added, and the aqueous layer wasextracted with CH₂Cl₂ (3×). The combined organic layers were dried(Na₂SO₄), filtered, and concentrated. The obtained residue was purifiedby trituration (hexanes) to afford the product (1.0 g, 62%).

¹H NMR (400 MHz, d₆-DMSO): δ 13.0 (s, 1H), 7.9-7.75 (m, 3H), 7.75-7.6(m, 1H), 4.9 (d, 1H), 4.45 (d, 1H), 3.9-3.7 (m, 2H), 3.3-3.1 (m, 2H),2.1-1. (m, 2H).

Step 4:7-[3-(3,5-Dichloro-4-fluoro-phenyl)-3-(trifluoromethyl)-2,4-dihydropyrrol-5-yl]-N-(1,1-dioxothietan-3-yl)indane-4-carboxamide(Compound 2-3)

To a solution of the product of step 3 (0.2 g), 1,1-dioxothietan-3-aminehydrochloride (0.08 g) and PyBroP (0.24 g) in CH₂Cl₂ (20 mL) at r.t. wasadded N,N-diisopropylethylamine (0.22 g). The reaction was stirred atr.t. overnight. Then, the reaction was diluted with CH₂C₁₂, washed withwater (2×), dried (Na₂SO₄), filtered and concentrated to give a residue,which was purified by flash chromatography on silica gel to afford theproduct (0.15 g, 55%).

¹H NMR (400 MHz, CDCl₃): δ 7.5 (m, 2H), 7.35 (m, 2H), 7.2 (m, 1H), 6.7(d, 1H), 5.0-4.85 (m, 2H), 4.7-4.6 (m, 2H), 4.45 (d, 1H), 4.1-4.0 (m,2H), 3.8 (d, 1H), 3.4 (d, 1H), 3.3-3.1 (m, 4H), 2.2-2.1 (m, 2H).

C.3 Compound Examples 3

Compound examples 3-1 to 3-13 correspond to compounds of formula C.3:

wherein R^(2a), R^(2b), R^(2c) and Y of each synthesized compound isdefined in one row of table C.3 below.

The compounds were synthesized in analogy to Synthesis Example S.3.

TABLE C.3 HPLC-MS: Method, R_(t) (min) & [M + H]⁺ Ex. R^(2a), R^(2b),R^(2c) —Y or ¹H-NMR (400 MHz, CDCl₃) 3-1 Cl, H, Cl —OCH₃ δ 7.64 (d, 1H),7.51 (s, 2H), 7.45 (s, 1H), 7.18 (d, 1H), 4.09 (d, 2H), 3.90 (s, 3H),3.73 (d, 1H), 3.08 (m, 2H), 2.94 (m, 2H), 1.86-1.72 (m, 4H) 3-2 Cl, H,Cl —OH ¹H NMR (400 MHz, CDCl₃): δ 7.87 (d, 1H), 7.65 (s, 2H), 7.50 (s,1H), 7.23 (d, 1H), 4.11 (d, 1H), 3.74 (d, 1H), 3.19 (m, 2H), 2.97 (m,2H), 1.82-1.81 (m, 4H). 3-3 Cl, H, Cl —NH-(1,1-dioxo-thietan-3-yl) A1.361 561.0 3-4 Cl, H, Cl —NHCH₂C(═O)NHCH₂CF₃ A 1.391 596.0 3-5 Cl, H,Cl —NHCH₂CF₃ A 1.466 539.0 3-6 Cl, H, Cl —NH-cyclopropyl A 1.424 497.03-7 Cl, H, Cl —NH-(thietan-3-yl) A 1.446 529.0 3-8 Cl, H, Cl—NHCH(CH₃)—C(═O)NHCH₂CF₃ A 1.400 610.0 3-9 Cl, H, Cl—NH-[(4R)-2-ethyl-3-oxo- A 1.379 570.0 isoxazolidin-4-yl] 3-10 Cl, H, Cl—NHCH₂-(thiazol-4-yl) A 1.389 554.0 3-11 Cl, H, Cl—NHCH₂-(2-pyrimidinyl) A 1.371 549.0 3-12 Cl, H, Cl —NHCH₂-(2-pyridyl) A1.243 548.0 3-13 Cl, H, Cl —NH-(1-oxo-thietan-3-yl) A 1.293 545.0

Synthesis Example S.38-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-(2,2,2-trifluoroethyl)tetralin-5-carboxamide

(Compound example 3-5; compound of formula C.3, wherein R^(2a) andR^(2c) are Cl, R^(2b) is H, and —Y is NHCH₂CF₃)

Step 1: 5-Methoxytetralin

To a mixture of tetralin-5-ol (32 g) and K₂CO₃ (64 g) in acetone (600mL) was added (CH₃)₂SO₄ (60 g), and the mixture was stirred at refluxfor 15 h. Then, the mixture was filtered and concentrated. The crudeproduct was purified by flash chromatography on silica gel (petroleumether/ethyl acetate) to afford the product (34 g, 88%).

¹H NMR (400 MHz, CDCl₃): δ 7.12 (m, 1H), 6.81-6.70 (m, 2H), 3.86 (s,3H), 2.81 (m, 2H), 2.71 (m, 2H), 1.91-1.77 (m, 4H).

Step 2: 1-(8-Methoxytetralin-5-yl)ethanone

At 0° C., acetyl chloride (“AcCl”, 16 g) was added dropwise to a mixtureof the product of step 1 (25 g) and AlCl₃ (28 g) in DCE (300 mL). Thereaction was stirred at 25° C. for 10 h, and then poured into ice water(200 mL). The aqueous layer was extracted with CH₂Cl₂ (3×300 mL), andthe combined organic layers were dried (Na₂SO₄), filtered andconcentrated to give the crude product (27 g) which was used in the nextstep without any further purification.

¹H NMR (400 MHz, CDCl₃): δ 7.64 (d, 1H), 6.71 (d, 1H), 3.89 (s, 3H),3.10-3.00 (m, 2H), 2.68 (m, 2H), 2.56 (s, 3H), 1.83-1.68 (m, 4H).

Step 3: 1-(8-Hydroxytetralin-5-yl)ethanone

The crude product of step 2 (30 g) in DCE (1.5 L) was treated with AlCl₃(30 g) and the mixture was stirred at 100° C. overnight. Then, thesolution was poured into ice water (500 mL) and extracted with CH₂Cl₂.The combined organic layers were dried (Na₂SO₄), filtered andconcentrated to give a residue, which was purified by flashchromatography on silica gel (petroleum ether/ethyl acetate) to affordthe product (15 g, 50%).

¹H NMR (400 MHz, CDCl₃): δ 7.56 (d, 1H), 6.69 (d, 1H), 3.06 (m, 2H),2.68 (m, 2H), 2.56 (s, 3H), 1.87-1.80 (m, 2H), 1.80-1.72 (m, 2H).

Step 4: (8-Acetyltetralin-5-yl) trifluoromethanesulfonate

To the product of step 3 (15 g) and Et₃N (20 g) in CH₂Cl₂ (500 mL) at 0°C. was added triflic anhydride (“Tf₂O”, 33 g). The mixture was stirredat 0° C. for 30 min. Then, the solution was poured onto ice water (500mL) and extracted with CH₂Cl₂. The combined organic layers were dried(Na₂SO₄), filtered and concentrated to give a residue, which waspurified by flash chromatography on silica gel (petroleum ether/ethylacetate) to afford the product (25 g, 95%).

¹H NMR (400 MHz, CDCl₃): δ 7.55-7.46 (m, 1H), 7.18 (m, 1H), 3.03-2.95(m, 2H), 2.84 (m, 2H), 2.58 (s, 3H), 1.91-1.79 (m, 4H).

Step 5: Methyl 8-acetyltetralin-5-carboxylate

To a solution of the product of step 4 (25 g) in methanol (500 mL) wereadded Na₂CO₃ (30 g) and[1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)(Pd(dppf)Cl₂, 3 g). The solution was pressurized with carbon monoxide(50 Psi) and heated at 50° C. overnight. Then, the mixture was filteredand the filtrate was concentrated. The residue was dissolved in CH₂Cl₂and washed with water, dried (Na₂SO₄), filtered and concentrated to givea residue, which was purified by flash chromatography on silica gel(petroleum ether/ethyl acetate) to afford the product (15 g, 65%).

¹H NMR (400 MHz, CDCl₃): δ 7.63 (d, 1H), 7.34 (d, 1H), 3.89 (s, 3H),3.04 (m, 2H), 2.92 (m, 2H), 2.57 (s, 3H), 1.77 (m, 4H).

Step 6: Methyl8-[3-(3,5-dichlorophenyl)-4,4,4-trifluoro-but-2-enoyl]tetralin-5-carboxylate

To a solution of the product of step 5 (10 g) and1-(3,5-dichlorophenyl)-2,2,2-trifluoro-ethanone (15.7 g, CAS130336-16-2) in DCE (100 mL) was added K₂CO₃ (5.9 g) and Et₃N (10 mL).The reaction was stirred for 16 h at 100° C. Then, the mixture wasfiltered and concentrated to give a residue, which was purified by flashchromatography on silica gel (petroleum ether/ethyl acetate) to affordthe product (17 g, 86%).

¹H NMR (400 MHz, CDCl₃): δ 7.66 (d, 1H), 7.38 (s, 2H), 7.34 (d, 1H),7.11 (m, 2H), 4.01 (s, 3H), 3.11-3.03 (m, 2H), 2.88 (m, 2H), 1.87-1.77(m, 4H).

Step 7: Methyl8-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]tetralin-5-carboxylate(Compound Examples 3-1)

To a solution of the product of step 2 (17 g) in DCE (500 mL) was addedhydroxylamine hydrochloride (5.3 g) and tetrabutylammoniumbromid(“TBAB”, 6.2 g), followed by drop wise addition of a solution of NaOH(6.1 g) in water (70 mL). The reaction was stirred for 12 h at 25° C.The organic layer was washed with water (3×100 mL), dried (Na₂SO₄),filtered and concentrated to give a residue, which was purified by flashchromatography on silica gel (petroleum ether/ethyl acetate) to affordthe product (12 g, 67%).

¹H NMR (400 MHz, CDCl₃): δ 7.64 (d, 1H), 7.51 (s, 2H), 7.45 (s, 1H),7.18 (d, 1H), 4.09 (d, 2H), 3.90 (s, 3H), 3.73 (d, 1H), 3.08 (m, 2H),2.94 (m, 2H), 1.86-1.72 (m, 4H).

Step 8:8-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]tetralin-5-carboxylicacid (Compound Examples 3-2)

The product of step 7 (12 g) in THF (100 mL) was treated with a solutionof LiOH (3 g) in water (30 mL), and the mixture stirred at r.t. for 12 hand at 80° C. for 5 h. Then, the pH of the reaction adjusted to pH 3using 1 M aqueous HCl solution. The aqueous layer was extracted withmethyl-tert-butylether (“MTBE”, 3×100 mL). The organic layers werecombined, dried (Na₂SO₄), filtered, and concentrated to afford theproduct (10 g, 88%).

¹H NMR (400 MHz, CDCl₃): δ 7.87 (d, 1H), 7.65 (s, 2H), 7.50 (s, 1H),7.23 (d, 1H), 4.11 (d, 1H), 3.74 (d, 1H), 3.19 (m, 2H), 2.97 (m, 2H),1.82-1.81 (m, 4H).

Step 9:8-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-(2,2,2-trifluoroethyl)tetralin-5-carboxamide

To a solution of the product of step 8 (0.3 g),2,2,2-trifluoroethylamine (0.08 g) and PyBroP (0.37 g) in CH₂Cl₂ (10 mL)at r.t. was added N,N-diisopropylethylamine (0.27 g). The reaction wasstirred at r.t. overnight. Then, the reaction was concentrated to give aresidue, which was purified by flash chromatography on silica gel toafford the product (0.19 g, 52%).

¹H NMR (400 MHz, CDCl₃): δ 7.55 (s, 2H), 7.45 (s, 1H), 7.2 (d, 1H), 7.1(d, 1H), 6.0 (m, 1H), 4.2-4.0 (m, 3H), 3.7 (d, 1H), 2.9 (m, 2H), 2.85(m, 2H), 1.8-1.7 (m, 4H).

C.4 Compound Examples 4

Compound examples 4-1 to 4-2 correspond to compounds of formula C.4:

wherein R¹¹¹, R²²² and Y of each compound is defined in one row of tableC.4 below.

The compounds 4-1 and 4-2 were obtained from the corresponding racemiccompound example 1-7 by separation using a preparative chiral HPLC(method B). Assignment of the absolute configuration was done by X-raycrystallography.

Method B (prepative chiral HPLC). Instrument: Thar SFC Pre-80. Column:Chiralpak AS-H 5 mm, 3.0 cm id×25 cm L Mobile phase: A for SFC CO₂ and Bfor MeOH (0.1% NH₄OH). Gradient: A:B=65:35. Flow rate: 70 mL/min.Detection wavelength: 220 nm. System Back Pressure: 100 bar.

Method C (analytical chiral HPLC). Instrument: Thar analytical SFC.Column: Chiralpak AS-H 5 mm, 0.46 cm id×15 cm L Mobile phase: A for SFCCO₂ and B for Methanol (0.05% Isopropylamine). Gradient: B in A from 10%to 40% in 5 minutes. Flow rate: 4.0 mL/min. Detection wavelength: 220nm. System Back Pressure: 100 bar.

TABLE C.4 Chiral analytical HPLC Method, Ex. R¹¹¹ R²²² —Y retention time4-1 3,5-Dichloro-4- CF₃ —NHCH₂-(2- C 2.78 min fluoro-phenyl pyrimidinyl)4-2 CF₃ 3,5-Dichloro-4- —NHCH₂-(2- C 3.44 min fluoro-phenyl pyrimidinyl)

C.5 Compound Examples 5

Compound examples 5-1 to 5-2 corresponds to compounds of formula C.5:

wherein R^(2a), R^(2b), R^(2c) R^(3a), R^(3b) and Y of each synthesizedcompound is defined in one row of table C.5 below.

The compounds were synthesized in analogy to Synthesis Example S.4.

TABLE C.5 HPLC-MS: Method, R_(t) (min) & Ex. R^(2a), R^(2b), R^(2c)R^(3a), R^(3b) —Y [M + H]⁺ or ¹H-NMR 5-1 Cl, F, Cl F, H —OCH₃ ¹H NMR(400 MHz, CDCl₃): δ 7.9 (d, 1H), 7.6 (m, 2H), 7.45 (d, 1H), 6.5 (d, 1H),3.9 (s, 3H), 3.35 (m, 2H), 3.2 (m, 2H), 2.15 (m, 2H) 5-2 Cl, F, Cl F, H—NHCH₂-(2-pyridyl) A 1.248 570.0

Synthesis Example S.47-[5-(3,5-Dichloro-4-fluoro-phenyl)-4-fluoro-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-(2-pyridylmethyl)indane-4-carboxamide

(Compound example 5-2; compound of formula C.5, wherein R^(2a) andR^(2c) are Cl, R^(2b) is F, R^(3a) is F and R^(3b) is H, and —Y is—NHCH₂—(2-pyridyl))

Step 1: Methyl7-[5-(3,5-dichloro-4-fluoro-phenyl)-4-fluoro-5-(trifluoromethyl)-4H-isoxazol-3-yl]indane-4-carboxylate(Compound Example 5-1)

To a solution of7-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]indane-4-carboxylate(compound example 1-1, 2 g) in THF (30 mL) under nitrogen at −78° C. wasadded), lithium hexamethyldisilazide (“LiHMDS”, 4.6 mL, 1 M solution inTHF) and the mixture was stirred for 1.5 h at −78° C. Then,N-fluorobenzenesulfonimide (“NFSI”, 1.7 g) was added at −78° C. in oneportion and the mixture was stirred at −78° C. for another 3 h. Then,the reaction was quenched with saturated aqueous NH₄Cl solution. Ethylacetate was added (300 mL) and the organic layer was washed with water(3×), dried (Na₂SO₄), filtered, and concentrated to afford a residuethat was purified by flash chromatography on silica gel (ethylacetate/cyclohexane) to afford the product (0.4 g, 19%).

¹H NMR (400 MHz, CDCl₃): δ 7.9 (d, 1H), 7.6 (m, 2H), 7.45 (d, 1H), 6.5(d, 1H), 3.9 (s, 3H), 3.35 (m, 2H), 3.2 (m, 2H), 2.15 (m, 2H).

Step 2:7-[5-(3,5-Dichloro-4-fluoro-phenyl)-4-fluoro-5-(trifluoromethyl)-4H-isoxazol-3-yl]indane-4-carboxylicacid

The product of step 1 (0.4 g) in THF (7.5 mL) was treated with asolution of LiOH (0.08 g) in water (2.5 mL), and the mixture stirred atr.t. overnight. Then, diethyl ether (300 mL) was added and the pH of thesolution was adjusted to pH 3-4 using 10% aqueous HCl solution. Theorganic layer was separated, washed with water (2×), dried (Na₂SO₄),filtered, and concentrated to afford the product (0.37 g, 95%), whichwas used in the next step without any further purification.

Step 3:7-[5-(3,5-Dichloro-4-fluoro-phenyl)-4-fluoro-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-(2-pyridylmethyl)indane-4-carboxamide(Compound Example 5-2)

To a solution of the product of step 2 (0.36 g), 2-picolylamine (0.1 g,CAS 3731-51-9) and PyBroP (0.42 g) in CH₂Cl₂ (40 mL) at r.t. was addedN,N-diisopropylethylamine (0.31 g). The reaction was stirred at r.t.overnight. Then, the reaction was quenched with water. The organic layerwas separated, dried (Na₂SO₄), filtered and concentrated to give aresidue, which was purified by flash chromatography on silica gel toafford the product (0.29 g, 68%).

HPLC-MS (method A): 1.248 min, M=570.0.

C.6 Compound Examples 6

Compound example 6-1 corresponds to a compound of formula C.6:

wherein R^(2a), R^(2b), R^(2c) and Y of each synthesized compound isdefined in one row of table C.6 below.

The compound was synthesized in analogy to Synthesis Example S.5.

TABLE C.6 HPLC-MS: Method, R_(t) (min) & [M + H]⁺ Ex. R^(2a), R^(2b),R^(2c) —Y or ¹H-NMR 6-1 Cl, H, Cl —NHCH₂-(2-pyridyl) A 1.248 570.0

Synthesis Example S.57-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-(2-pyridylmethyl)indane-4-carbothioamide

(Compound example 6-1; compound of formula C.5, wherein R^(2a) andR^(2c) are Cl, R^(2b) is H, and —Y is —NHCH₂-(2-pyridyl))

A solution of7-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-(2-pyridylmethyl)indane-4-carboxamide(compound example 1-27, 190 mg) and Lawesson's reagent (90 mg, CAS19172-47-5) in toluene (15 mL) was refluxed for 5 h and then stirred atr.t. overnight. Ethyl acetate was added (200 mL) and the organic layerwas washed with water (3×), dried (Na₂SO₄), filtered and concentrated togive a residue, which was purified by flash chromatography on silica gelto afford the product (70 mg, 60%).

HPLC-MS (method A): 1.335 min, M=550.0.

II. Evaluation of Pesticidal Activity

The activity of the compounds of formula I of the present invention canbe demonstrated and evaluated by the following biological test.

B.1 Diamond Back Moth (Plutella xylostella)

The active compound was dissolved at the desired concentration in amixture of 1:1 (vol:vol) distilled water:aceteone. Surfactant (KineticHV) was added at a rate of 0.01% (vol/vol). The test solution wasprepared at the day of use.

Leaves of cabbage were dipped in test solution and air-dried. Treatedleaves were placed in petri dishes lined with moist filter paper andinoculated with ten 3^(rd) instar larvae. Mortality was recorded 72hours after treatment.

In this test, the compounds 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9,1-10, 1-11, 1-12, 1-13, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19, 1-20, 1-21,1-22, 1-23, 1-24, 1-25, 1-26, 1-27, 1-28, 1-29, 1-30, 1-31, 1-32, 1-33,1-34, 1-35, 1-36, 1-37, 1-38, 1-39, 1-40, 1-41, 1-42, 1-43, 1-44, 1-45,1-46, 1-47, 1-48, 1-49, 1-50, 1-51, 1-52, 1-53, 1-54, 1-55, 1-57, 1-58,1-59, 1-60, 1-61, 1-62, 1-63, 1-64, 1-65, 1-66, 1-67, 1-69, 1-70, 1-71,1-72, 2-1, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9, 2-10, 2-11, 2-12, 2-13,2-14, 2-17, 2-18, 2-19, 2-20, 2-21, 2-22, 2-23, 2-24, 3-3, 3-4, 3-5,3-6, 4-1, 4-2 at 300 ppm, respectively, showed a mortality of at least75% in comparison with untreated controls.

B.2 Green Peach Aphid (Myzus persicae)

For evaluating control of green peach aphid (Myzus persicae) throughsystemic means the test unit consisted of 96-well-microtiter platescontaining liquid artificial diet under an artificial mem brane.

The compounds were formulated using a solution containing 75% v/v waterand 25% v/v DMSO. Different concentrations of formulated compounds werepipetted into the aphid diet, using a custom built pipetter, at tworeplications.

After application, 5-8 adult aphids were placed on the artificialmembrane inside the microtiter plate wells. The aphids were then allowedto suck on the treated aphid diet and incubated at about 23±1° C. andabout 50±5% relative humidity for 3 days. Aphid mortality and fecunditywas then visually assessed.

In this test, the compounds 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10,1-11, 1-12, 1-13, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19, 1-20, 1-21, 1-22,1-23, 1-24, 1-25, 1-26, 1-27, 1-28, 1-29, 1-30, 1-31, 1-32, 1-33, 1-34,1-35, 1-36, 1-37, 1-38, 1-39, 1-40, 1-41, 1-42, 1-43, 1-44, 1-45, 1-46,1-47, 1-48, 1-49, 1-50, 1-51, 1-52, 1-53, 1-54, 1-55, 1-57, 1-58, 1-59,1-60, 1-61, 1-62, 1-63, 1-64, 1-65, 1-66, 1-67, 1-69, 1-70, 1-71, 1-72,1-73, 1-74, 1-75, 1-76, 1-77, 1-78, 1-79, 1-80, 1-82, 2-1, 2-2, 2-3,2-4, 2-5, 2-6, 2-7, 2-8, 2-9, 2-10, 2-11, 2-12, 2-13, 2-14, 2-17, 2-18,2-19, 2-20, 2-21, 2-22, 2-23, 2-24, 3-3, 3-4, 3-5, 3-6, 3-7, 3-8, 3-9,3-10, 3-11, 3-12, 3-13, 4-1, 4-2 at 2500 ppm, respectively, showed amortality of at least 75% in comparison with untreated controls.

B.3 Vetch Aphid (Megoura viciae)

For evaluating control of vetch aphid (Megoura viciae) through contactor systemic means the test unit consisted of 24-well-microtiter platescontaining broad bean leaf disks.

The compounds were formulated using a solution containing 75% v/v waterand 25% v/v DMSO. Different concentrations of formulated compounds weresprayed onto the leaf disks at 2.5 μl, using a custom built microatomizer, at two replications.

After application, the leaf disks were air-dried and 5-8 adult aphidsplaced on the leaf disks inside the microtiter plate wells. The aphidswere then allowed to suck on the treated leaf disks and incubated atabout 23±1° C. and about 50±5% relative humidity for 5 days. Aphidmortality and fecundity was then visually assessed.

In this test, the compounds 1-1, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9,1-10, 1-11, 1-12, 1-13, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19, 1-20, 1-21,1-22, 1-23, 1-24, 1-25, 1-26, 1-27, 1-28, 1-29, 1-30, 1-31, 1-32, 1-33,1-34, 1-35, 1-36, 1-37, 1-38, 1-39, 1-40, 1-41, 1-42, 1-43, 1-44, 1-45,1-46, 1-47, 1-48, 1-49, 1-50, 1-51, 1-52, 1-53, 1-54, 1-55, 1-57, 1-58,1-59, 1-60, 1-61, 1-62, 1-63, 1-64, 1-65, 1-66, 1-67, 1-69, 1-70, 1-71,1-72, 1-73, 1-74, 1-75, 1-76, 1-77, 1-78, 1-79, 1-80, 1-82, 2-2, 2-3,2-4, 2-5, 2-6, 2-7, 2-8, 2-9, 2-10, 2-11, 2-12, 2-13, 2-14, 2-17, 2-18,2-19, 2-20, 2-21, 2-22, 2-23, 2-24, 3-3, 3-4, 3-5, 3-6, 3-7, 3-8, 3-9,3-10, 3-11, 3-12, 3-13, 4-1, 4-2 at 2500 ppm, respectively, showed amortality of at least 75% in comparison with untreated controls.

B.4 Tobacco Budworm (Heliothis virescens)

For evaluating control of tobacco budworm (HeliothiS virescens) the testunit consisted of 96-well-microtiter plates containing an insect dietand 15-25 H. virescens eggs.

The compounds were formulated using a solution containing 75% v/v waterand 25% v/v DMSO. Different concentrations of formulated compounds weresprayed onto the insect diet at 10 μl, using a custom built microatomizer, at two replications.

After application, microtiter plates were incubated at about 28±1° C.and about 80±5% relative humidity for 5 days. Egg and larval mortalitywas then visually assessed.

In this test, the compounds 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9,1-10, 1-11, 1-12, 1-13, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19, 1-20, 1-21,1-22, 1-23, 1-24, 1-25, 1-26, 1-27, 1-28, 1-29, 1-30, 1-31, 1-32, 1-33,1-34, 1-35, 1-36, 1-37, 1-38, 1-39, 1-40, 1-41, 1-42, 1-43, 1-44, 1-45,1-46, 1-47, 1-48, 1-49, 1-50, 1-51, 1-52, 1-53, 1-54, 1-55, 1-57, 1-58,1-59, 1-60, 1-61, 1-62, 1-63, 1-64, 1-65, 1-66, 1-67, 1-68, 1-69, 1-70,1-71, 1-72, 1-73, 1-74, 1-75, 1-76, 1-77, 1-78, 1-79, 1-80, 1-82, 2-1,2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9, 2-10, 2-11, 2-12, 2-13, 2-14,2-17, 2-18, 2-19, 2-20, 2-21, 2-22, 2-23, 2-24, 3-3, 3-4, 3-5, 3-6, 3-7,3-8, 3-9, 3-10, 3-11, 3-12, 3-13, 4-1, 4-2 at 2500 ppm, respectively,showed a mortality of at least 75% in comparison with untreatedcontrols.

B.5 Boll Weevil (Anthonomus grandis)

For evaluating control of boll weevil (Anthonomus grandis) the test unitconsisted of 96-well-microtiter plates containing an insect diet and5-10 A. grandis eggs.

The compounds were formulated using a solution containing 75% v/v waterand 25% v/v DMSO. Different concentrations of formulated compounds weresprayed onto the insect diet at 5 μl, using a custom built microatomizer, at two replications.

After application, microtiter plates were incubated at about 25±1° C.and about 75±5% relative humidity for 5 days. Egg and larval mortalitywas then visually assessed.

In this test, the compounds 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9,1-10, 1-11, 1-12, 1-13, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19, 1-20, 1-21,1-22, 1-23, 1-24, 1-25, 1-26, 1-27, 1-28, 1-29, 1-30, 1-31, 1-32, 1-33,1-34, 1-35, 1-36, 1-37, 1-38, 1-39, 1-40, 1-41, 1-42, 1-43, 1-44, 1-45,1-46, 1-47, 1-48, 1-49, 1-50, 1-51, 1-52, 1-53, 1-54, 1-55, 1-57, 1-58,1-59, 1-60, 1-61, 1-62, 1-63, 1-64, 1-65, 1-66, 1-67, 1-69, 1-70, 1-71,1-72, 1-73, 1-74, 1-75, 1-76, 1-77, 1-78, 1-79, 1-80, 1-81, 1-82, 2-1,2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9, 2-10, 2-11, 2-12, 2-13, 2-14,2-16, 2-17, 2-18, 2-19, 2-20, 2-21, 2-22, 2-23, 2-24, 3-2, 3-3, 3-4,3-5, 3-6, 3-7, 3-8, 3-9, 3-10, 3-11, 3-12, 3-13, 4-1, 4-2 at 2500 ppm,respectively, showed a mortality of at least 75% in comparison withuntreated controls.

B.6 Mediterranean Fruitfly (Ceratitis capitata)

For evaluating control of Mediterranean fruitfly (CeratitiS capitata)the test unit consisted of microtiter plates containing an insect dietand 50-80 C. capitata eggs. The compounds were formulated using asolution containing 75% v/v water and 25% v/v DMSO. Differentconcentrations of formulated compounds were sprayed onto the insect dietat 5 μl, using a custom built micro atomizer, at two replications.

After application, microtiter plates were incubated at about 28±1° C.and about 80±5% relative humidity for 5 days. Egg and larval mortalitywas then visually assessed.

In this test, the compounds 1-1, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9,1-10, 1-11, 1-12, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19, 1-20, 1-21, 1-22,1-23, 1-24, 1-25, 1-26, 1-27, 1-28, 1-29, 1-30, 1-31, 1-32, 1-33, 1-34,1-35, 1-36, 1-37, 1-38, 1-39, 1-40, 1-41, 1-42, 1-43, 1-44, 1-45, 1-46,1-47, 1-48, 1-49, 1-50, 1-51, 1-52, 1-53, 1-54, 1-55, 1-57, 1-58, 1-59,1-60, 1-61, 1-62, 1-63, 1-64, 1-65, 1-66, 1-67, 1-69, 1-70, 1-71, 1-72,1-73, 1-74, 1-75, 1-76, 1-77, 1-78, 1-79, 1-80, 1-82, 2-3, 2-4, 2-5,2-6, 2-7, 2-8, 2-9, 2-10, 2-11, 2-12, 2-13, 2-14, 2-16, 2-17, 2-18,2-19, 2-20, 2-21, 2-22, 2-23, 2-24, 3-3, 3-4, 3-5, 3-6, 3-7, 3-8, 3-9,3-10, 3-11, 3-12, 3-13, 4-1, 4-2 at 2500 ppm showed a mortality of atleast 75% in comparison with untreated controls.

B.7 Orchid Thrips (dichromothrips corbetti)

Dichromothrips corbetti adults used for bioassay were obtained from acolony maintained continuously under laboratory conditions. For testingpurposes, the test compound is diluted in a 1:1 mixture of acetone:water(vol:vol), plus Kinetic HV at a rate of 0.01% v/v.

Thrips potency of each compound was evaluated by using afloral-immersion technique. All petals of individual, intact orchidflowers were dipped into treatment solution and allowed to dry in Petridishes. Treated petals were placed into individual re-sealable plasticalong with about 20 adult thrips. All test arenas were held undercontinuous light and a temperature of about 28° C. for duration of theassay. After 3 days, the numbers of live thrips were counted on eachpetal. The percent mortality was recorded 72 hours after treatment.

In this test, the compounds 1-1, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9,1-10, 1-11, 1-12, 1-13, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19, 1-20, 1-21,1-22, 1-23, 1-24, 1-25, 1-26, 1-27, 1-28, 1-29, 1-30, 1-31, 1-32, 1-33,1-34, 1-35, 1-36, 1-37, 1-38, 1-39, 1-40, 1-41, 1-42, 1-43, 1-44, 1-45,1-46, 1-47, 1-48, 1-49, 1-50, 1-51, 1-52, 1-53, 1-54, 1-55, 1-57, 1-58,1-59, 1-60, 1-61, 1-62, 1-63, 1-64, 1-65, 1-66, 1-67, 1-68, 1-69, 1-70,1-71, 1-72, 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9, 2-10, 2-11, 2-12,2-13, 2-14, 2-17, 2-18, 2-19, 2-20, 2-21, 2-22, 2-23, 2-24, 3-3, 3-4,3-5, 3-6, 4-1, 4-2 at 300 ppm, respectively, showed a mortality of atleast 75% in comparison with untreated controls.

B.8 Rice Green Leafhopper (Nephotettix virescens)

Rice seedlings were cleaned and washed 24 hours before spraying. Theactive compounds were formulated in 1:1 acetone:water (vol:vol), and0.01% vol/vol surfactant (Kinetic HV) was added. Potted rice seedlingswere sprayed with 5-6 ml test solution, air dried, covered with Mylarcages cages and inoculated with 10 adults. Treated rice plants were keptat about 28-29° C. and relative humidity of about 50-60%. Percentmortality was recorded after 72 hours.

In this test, the compounds 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10,1-11, 1-12, 1-13, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19, 1-20, 1-21, 1-22,1-23, 1-25, 1-26, 1-27, 1-28, 1-29, 1-30, 1-31, 1-32, 1-33, 1-34, 1-35,1-36, 1-38, 1-39, 1-40, 1-41, 1-42, 1-43, 1-44, 1-45, 1-46, 1-47, 1-48,1-49, 1-50, 1-51, 1-52, 1-53, 1-54, 1-55, 1-57, 1-58, 1-59, 1-60, 1-61,1-62, 1-63, 1-64, 1-65, 1-66, 1-67, 1-69, 1-70, 1-71, 1-72, 2-3, 2-4,2-5, 2-6, 2-7, 2-8, 2-9, 2-10, 2-11, 2-12, 2-13, 2-14, 2-17, 2-18, 2-19,2-20, 2-21, 2-23, 2-24, 3-3, 3-4, 3-5, 3-6, 4-2 at 300 ppm,respectively, showed a mortality of at least 75% in comparison withuntreated controls.

B.9 Red Spider Mite (Tetranychus kanzawai)

The active compound was dissolved at the desired concentration in amixture of 1:1 (vol:vol) distilled water:acetone. Add surfactant(Kinetic HV) was added at a rate of 0.01% (vol/vol). The test solutionwas prepared at the day of use.

Potted cowpea beans of 4-5 days of age were cleaned with tap water andsprayed with 1-2 ml of the test solution using air driven hand atomizer.The treated plants were allowed to air dry and afterwards inoculatedwith 30 or more mites by clipping a cassava leaf section from rearingpopulation. Treated plants were placed inside a holding room at about25-27° C. and about 50-60% relative humidity. Percent mortality wasassessed 72 hours after treatment.

In this test, the compounds 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10,1-11, 1-12, 1-13, 1-14, 1-18, 1-20, 1-21, 1-22, 1-23, 1-26, 1-27, 1-28,1-29, 1-30, 1-31, 1-32, 1-33, 1-34, 1-35, 1-36, 1-38, 1-39, 1-40, 1-41,1-42, 1-43, 1-44, 1-45, 1-46, 1-47, 1-48, 1-49, 1-50, 1-51, 1-52, 1-53,1-54, 1-55, 1-57, 1-58, 1-59, 1-60, 1-61, 1-62, 1-63, 1-64, 1-65, 1-66,1-67, 1-69, 1-70, 1-71, 1-72, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9, 2-10,2-11, 2-12, 2-13, 2-14, 2-17, 2-18, 2-19, 2-20, 2-21, 2-22, 2-23, 2-24,3-3, 3-4, 3-5, 3-6, 4-2 at 300 ppm showed a mortality of at least 75% incomparison with untreated controls.

B.10 Southern Armyworm (Spodoptera eridania)

The active compounds were formulated in cyclohexanone as a 10,000 ppmsolution supplied in tubes. The tubes were inserted into an automatedelectrostatic sprayer equipped with an atomizing nozzle and they servedas stock solutions for which lower dilutions were made in 50%acetone:50% water (v/v). A nonionic surfactant (Kinetic®) was includedin the solution at a volume of 0.01% (v/v).

Lima bean plants (variety Sieva) were grown 2 plants to a pot andselected for treatment at the 1^(st) true leaf stage. Test solutionswere sprayed onto the foliage by an automated electrostatic plantsprayer equipped with an atomizing spray nozzle. The plants were driedin the sprayer fume hood and then removed from the sprayer. Each pot wasplaced into perforated plastic bags with a zip closure. About 10 to 11armyworm larvae were placed into the bag and the bags zipped closed.Test plants were maintained in a growth room at about 25° C. and about20-40% relative humidity for 4 days, avoiding direct exposure tofluorescent light (24 hour photoperiod) to prevent trapping of heatinside the bags. Mortality and reduced feeding were assessed 4 daysafter treatment, compared to untreated control plants.

In this test, the compounds 1-5, 1-6, 1-7, 1-10, 1-12, 1-14, 1-16, 1-17,1-21, 1-23, 1-25, 1-26, 1-27, 1-28, 1-29, 1-30, 1-31, 1-32, 1-33, 1-34,1-38, 1-42, 1-49, 1-51, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9, 2-10, 2-11,2-12, 2-13, 2-14, 4-2 at 1 ppm showed a mortality of at least 75% incomparison with untreated controls.

B.11 Green Soldier Stink Bug (Nezara viridula)

The active compound was dissolved at the desired concentration in amixture of 1:1 (vol:vol) distilled water:acetone. Surfactant (KineticHV) was added at a rate of 0.01% (vol/vol). The test solution wasprepared at the day of use.

Soybean pods were placed in glass Petri dishes lined with moist filterpaper and inoculated with ten late 3rd instar N. viridula. Using a handatomizer, approximately 2 ml solution is sprayed into each Petri dish.Assay arenas were kept at about 25° C. Percent mortality was recordedafter 5 days.

In this test, the compounds 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10,1-11, 1-12, 1-13, 1-14, 1-15, 1-16, 1-17, 1-18, 1-20, 1-21, 1-22, 1-23,1-25, 1-26, 1-27, 1-28, 1-29, 1-3, 1-30, 1-31, 1-32, 1-33, 1-34, 1-35,1-36, 1-38, 1-39, 1-40, 1-41, 1-42, 1-44, 1-45, 1-46, 1-47, 1-48, 1-49,1-50, 1-51, 1-53, 1-54, 1-55, 1-57, 1-58, 1-59, 1-60, 1-61, 1-62, 1-63,1-64, 1-65, 1-66, 1-67, 1-72, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9, 2-10,2-11, 2-12, 2-13, 2-14, 2-17, 2-18, 2-19, 2-20, 2-21, 2-22, 2-23, 2-24,3-3, 3-4, 4-2 at 300 ppm showed a mortality of at least 75% incomparison with untreated controls.

B.12 Neotropical Brown Stink Bug (Euschistus heros)

The active compound was dissolved at the desired concentration in amixture of 1:1 (vol:vol) distilled water: acetone. Surfactant (KineticHV) was added at a rate of 0.01% (vol/vol). The test solution wasprepared at the day of use.

Soybean pods were placed in microwavable plastic cups and inoculatedwith ten adult stage E. heros. Using a hand atomizer, approximately 1 mlsolution is sprayed into each cup, insects and food present. A watersource was provided (cotton wick with water). Each treatment wasreplicated 2-fold. Assay arenas were kept at about 25° C. Percentmortality was recorded after 5 days.

In this test, the compounds 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10,1-11, 1-12, 1-13, 1-14, 1-17, 1-18, 1-20, 1-21, 1-23, 1-25, 1-26, 1-27,1-28, 1-30, 1-31, 1-32, 1-33, 2-3, 2-4, 2-6, 2-7, 2-8, 2-9, 2-10, 2-11at 100 ppm showed a mortality of at least 75% in comparison withuntreated controls.

B.13 Brown Marmorated Stink Bug (Halyomorpha halys)

The active compound was dissolved at the desired concentration in amixture of 1:1 (vol:vol) distilled water: acetone. Surfactant (KineticHV) was added at a rate of 0.01% (vol/vol). The test solution wasprepared at the day of use.

Row peanuts and soybean seeds were placed into microwavable plastic cupsand inoculated with five adult stage H. halys. Using a hand atomizer,approximately 1 ml solution is sprayed into each cup, insects and foodpresent. A water source was provided (cotton wick with water). Eachtreatment is replicated 4-fold. Assay arenas are kept at about 25° C.Percent mortality was recorded after 5 days.

In this test, the compounds 1-3, 1-4, 1-5, 1-6, 1-7, 1-9, 1-11, 1-12,1-14, 1-16, 1-20, 1-21, 1-25, 1-26, 1-27, 1-28, 1-30, 1-31, 1-32, 1-33,2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9, 2-10 at 100 ppm showed a mortality ofat least 75% in comparison with untreated controls.

1.-24. (canceled)
 25. A method for treating or protecting an animal from infestation or infection by invertebrate pests, which method comprises contacting the animal with a parasiticidally or pesticidally effective amount of at least one compound of the formula I:

or an N-oxide, stereoisomer or veterinarily acceptable salt thereof; wherein X¹ is O or CH₂; A is a group of following formula:

wherein # denotes the bond to the aromatic ring of formula (I); W is selected from O and S; Y is selected from hydrogen, —N(R⁵)R⁶ and —OR⁹; B¹, B² and B³ are each independently CR²; G¹ and G² are each independently CR⁴; R^(g1) and R^(g2) form together a bridging group selected from —CH₂CH₂CH₂CH₂— and —CH₂CH₂CH₂—; R¹ is CF₃; each R² is independently selected from the group consisting of hydrogen, halogen, C₁-C₂-haloalkoxy and C₁-C₂-haloalkyl; R^(3a), R^(3b) are each independently selected from the group consisting of hydrogen, halogen, hydroxyl, —CO₂R^(3d), C₁-C₃-alkyl, C₁-C₃-haloalkyl, C₂-C₃-alkenyl, C₂-C₃-alkynyl, C₁-C₃-alkoxy, C₁-C₃-haloalkoxy, C₁-C₃-alkylthio, C₁-C₃-haloalkylthio, C₁-C₃-alkylsulfonyl and C₁-C₃-haloalkylsulfonyl; or R^(3a) and R^(3b) together form a group ═O, ═C(R^(3c))₂, ═NOH or ═NOCH₃; each R^(3c) is independently selected from the group consisting of hydrogen, halogen, CH₃ and CF₃; R^(3d) is selected from the group consisting of hydrogen, C₁-C₆-alkyl and C₁-C₃-alkyloxy-C₁-C₃-alkyl-; each R⁴ is independently selected from the group consisting of hydrogen, halogen and cyano; R⁵ selected from hydrogen, C₁-C₆-alkyl, C₂-C₃-alkynyl and CH₂—CN; R⁶ is selected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₄-alkyl which carries one radical R⁸, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl which may be substituted by 1 or 2 substituents selected from F, CN and pyridyl; —N(R^(101a))R^(101b), wherein R^(101a) is selected from hydrogen and C₁-C₆-alkyl; and R^(101b) is selected from hydrogen, —C(═O)N(R^(14a))R^(14b), wherein R^(14a) is selected from the group consisting of hydrogen and C₁-C₆-alkyl; and R^(14b) is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₂-C₄-alkynyl, CH₂—CN, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; phenyl, optionally substituted with 1, 2, 3, 4 or 5 substituents R¹⁶, and a heterocyclic ring selected from rings of formulae E-1 to E-42

where in these rings E-1 to E-42 as a meaning for R^(101b) the zigzag line denotes the attachment point to the remainder of the molecule;  k is 0, 1, 2 or 3, and each R¹⁶ is independently selected from the group consisting of halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-haloalkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl, aminocarbonyl, C₁-C₄-alkylaminocarbonyl and di-(C₁-C₄-alkyl)aminocarbonyl; CH═NOR^(9a), wherein R^(9a) is selected from hydrogen, C₁-C₆-alkyl and C₁-C₆-haloalkyl; phenyl which may be substituted with 1, 2, 3, 4, or 5 substituents R¹¹, and a 3-, 4-, 5- or 6-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO₂, as ring members, where the heteromonocyclic ring may be substituted with one or more substituents R¹¹; wherein each R¹¹ is independently selected from the group consisting of halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl and C₂-C₄-haloalkynyl; or two R¹¹ present on the same carbon atom of a saturated heterocyclic ring may form together ═O or ═S; or two R¹¹ present on the same S or SO ring member of a heterocyclic ring may together form a group ═N(C₁-C₆-alkyl), ═NO(C₁-C₆-alkyl), ═NN(H)(C₁-C₆-alkyl) or ═NN(C₁-C₆-alkyl)₂; each R⁸ is independently selected from OH, CN, C₃-C₈-cycloalkyl which optionally carries a CN or a C₁-C₂-haloalkyl substituent; C₃-C₈-halocycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, —C(═O)N(R^(102a))R^(102b), phenyl, optionally substituted with 1, 2, 3, 4 or 5 substituents R¹⁶, and a 3-, 4-, 5- or 6-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic ring containing 1, 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO₂, as ring members, where the heteromonocyclic ring may be substituted with one or more substituents R¹⁶; wherein R^(102a) is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₂-C₃-alkynyl and CH₂—CN; R^(102b) is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, CH₂—CN, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₃-C₆-cycloalkylmethyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, phenyl which is optionally substituted with 1, 2, 3, 4 or 5 substituents selected from the group consisting of halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio and C₁-C₄-haloalkylthio; and a heterocyclic ring selected from rings of formulae E-1 to E-42 as defined above and E-43 to E-57:

where in these rings E-43 to E-57 the zigzag line denotes the attachment point to the remainder of the molecule;  k is 0, 1, 2 or 3, n is 0, 1 or 2; and each R¹⁶ is independently selected from the group consisting of halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-haloalkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl, aminocarbonyl, C₁-C₄-alkylaminocarbonyl and di-(C₁-C₄-alkyl)aminocarbonyl; or two R¹⁶ present on the same carbon atom of a saturated ring may form together ═O or ═S; and each R¹⁶ as a substituent on phenyl (as a meaning of R⁸) or the heterocyclic rings (as a meaning of R⁸) is independently selected from the group consisting of halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl and C₂-C₄-haloalkynyl; or two R¹⁶ present on the same carbon atom of a saturated heterocyclic ring may form together ═O or ═S; or two R¹⁶ present on the same S or SO ring member of a heterocyclic ring may together form a group ═N(C₁-C₆-alkyl), ═NO(C₁-C₆-alkyl), ═NN(H)(C₁-C₆-alkyl) or ═NN(C₁-C₆-alkyl)₂; or R⁵ and R⁶, together with the nitrogen atom to which they are bound, form a 5- or 6-membered saturated heterocyclic ring, where the ring may further contain 1 or 2 heteroatoms or heteroatom-containing groups selected from O, S, SO, SO₂, NH and C═O as ring members, wherein the heterocyclic ring may be substituted with 1, 2 or 3 substituents independently selected from the group consisting of halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy; or R⁵ and R⁶ together form a group ═S(R^(9b))₂, where R^(9b) is selected from C₁-C₆-alkyl and C₁-C₆-haloalkyl; R⁹ is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl and C₁-C₆-alkyl substituted by one radical R¹³; where R¹³ is selected from CN, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl and a heterocyclic ring selected from rings of formulae E-1 to E-57 as defined above; where in these rings E-1 to E-57 as a meaning of R¹³ the zigzag line denotes the attachment point to the remainder of the molecule; k is 0, 1, 2 or 3, n is 0, 1 or 2; and each R¹⁶ is independently selected from the group consisting of halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-haloalkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl, aminocarbonyl, C₁-C₄-alkylaminocarbonyl and di-(C₁-C₄-alkyl)aminocarbonyl; or two R¹⁶ present on the same carbon atom of a saturated ring may form together ═O or ═S; and each R¹⁶ in all other cases is independently selected from the group consisting of halogen, nitro, cyano, —OH, —SH, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-haloalkoxycarbonyl, aminocarbonyl, C₁-C₄-alkylaminocarbonyl, di-(C₁-C₄-alkyl)-aminocarbonyl, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl; C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the three last-mentioned aliphatic radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2 radicals selected from cyano, C₃-C₄-cycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy and oxo; C₃-C₈-cycloalkyl which may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2 radicals selected from cyano, C₁-C₄-alkyl, C₃-C₄-cycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy and oxo; phenyl, benzyl, pyridyl and phenoxy, wherein the four last mentioned radicals may be unsubstituted, partially or fully halogenated and/or carry 1, 2 or 3 substituents selected from C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy and (C₁-C₆-alkoxy)carbonyl; or two R¹⁶ present together on the same atom of an unsaturated or partially unsaturated ring may be ═O, ═S, ═N(C₁-C₆-alkyl), ═NO(C₁-C₆-alkyl), ═CH(C₁-C₄-alkyl) or ═C(C₁-C₄-alkyl)C₁-C₄-alkyl; or or two R¹⁶ present on the same S or SO ring member of a heterocyclic ring may together form a group ═N(C₁-C₆-alkyl), ═NO(C₁-C₆-alkyl), ═NN(H)(C₁-C₆-alkyl) or ═NN(C₁-C₆-alkyl)₂; or two R¹⁶ on two adjacent carbon atoms form together with the carbon atoms they are bonded to a 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated ring, wherein the ring may contain 1 or 2 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO₂, as ring members, and wherein the ring optionally carries one or more substituents selected from halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy.
 26. The method of claim 25, where each R⁸ is independently selected from OH, CN, C₃-C₈-cycloalkyl which optionally carries a CN or CF₃ substituent, C₃-C₈-halocycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, —C(═O)N(R^(102a))R^(102b), phenyl, optionally substituted with 1, 2, 3, 4 or 5 substituents R¹⁶, and a 3-, 4-, 5- or 6-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO₂, as ring members, where the heteromonocyclic ring may be substituted with one or more substituents R¹⁰⁶; where R^(102a), R^(102b) and R¹⁶ are as defined in claim
 25. 27. The method of claim 25, where X¹ is O.
 28. The method of claim 25, where X¹ is CH₂.
 29. The method of claim 25, where W is O.
 30. The method of claim 25, where in A Y is —OR⁹.
 31. The method of claim 25, where in A Y is —N(R⁵)R⁶; wherein R⁵ and R⁶ are as defined in claim
 25. 32. The method of claim 31, where R⁵ is hydrogen or C₁-C₃-alkyl; R⁶ is selected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₄-alkyl which carries one radical R⁸, wherein R⁸ is as defined below; C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl which may be substituted by 1 or 2 substituents selected from F, CN and pyridyl; —N(R^(101a))R^(101b), wherein R^(101a) is selected from hydrogen and C₁-C₆-alkyl; and R^(101b) is selected from hydrogen, —C(═O)N(R^(14a))R^(14b), wherein R^(14a) is selected from the group consisting of hydrogen and C₁-C₆-alkyl; and R^(14b) is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₂-C₄-alkynyl, CH₂—CN, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; phenyl, optionally substituted with 1, 2, 3, 4 or 5 substituents R¹⁶, wherein R¹⁶ is as defined below; and a heteroaromatic ring selected from rings of formulae E-1 to E-42 as defined in claim 25; —CH═NOR^(9a), wherein R^(9a) is selected from hydrogen, C₁-C₆-alkyl and C₁-C₆-haloalkyl; phenyl which may be substituted with 1, 2, 3, 4, or 5 substituents R¹¹, wherein R¹¹ is as defined below; and a heteromonocyclic ring selected from rings of formulae F-1 to F-60

wherein the zigzag line denotes the attachment point to the remainder of the molecule; k is 0, 1, 2 or 3, n is 0, 1 or 2, and each R¹¹ is independently selected from the group consisting of halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-haloalkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl, aminocarbonyl, C₁-C₄-alkylaminocarbonyl and di-(C₁-C₄-alkyl)-aminocarbonyl; or two R¹¹ present on the same carbon atom of a saturated or partially unsaturated heterocyclic ring may form together ═O or ═S; or two R¹¹ present on the same S or SO ring member of a heterocyclic ring may together form a group ═N(C₁-C₆-alkyl), ═NO(C₁-C₆-alkyl), ═NN(H)(C₁-C₆-alkyl) or ═NN(C₁-C₆-alkyl)₂; R⁸ is selected from OH, CN, C₃-C₈-cycloalkyl which optionally carries a CN, CHF₂ or CF₃ substituent, C₃-C₈-halocycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, —C(═O)N(R^(102a))R^(102b), phenyl, optionally substituted with 1, 2, 3, 4 or 5 substituents R¹⁶ and a heterocyclic ring selected from rings of formulae E-1 to E-57 as defined in claim 25 and additionally from 1,3-dioxolan-2-yl which may carry 1, 2 or 3 substituents R¹⁶ as defined in claim 25; wherein R^(102a) is selected from the group consisting of hydrogen and C₁-C₆-alkyl; R^(102b) is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, CH₂—CN, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy; and each R¹⁶ as a substituent on phenyl or heterocyclic rings of formulae E-1 to E-57 is independently selected from the group consisting of halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-haloalkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl, aminocarbonyl, C₁-C₄-alkylaminocarbonyl and di-(C₁-C₄-alkyl)-aminocarbonyl; or two R¹⁶ present on the same carbon atom of a saturated heterocyclic ring may form together ═O or ═S; or two R¹⁶ present on the same S or SO ring member of a heterocyclic ring may together form a group ═N(C₁-C₆-alkyl), ═NO(C₁-C₆-alkyl), ═NN(H)(C₁-C₆-alkyl) or ═NN(C₁-C₆-alkyl)₂.
 33. The method of claim 32, where R⁵ is as defined in claim 32; R⁶ is selected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₄-alkyl which carries one radical R⁸, wherein R⁸ is as defined below; C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl which may be substituted by 1 or 2 substituents selected from F, CN and pyridyl; —N(R^(101a))R^(101b), wherein R^(101a) and R^(101b) are as defined in claim 32; —CH═NOR^(9a), wherein R^(9a) is as defined in claim 32; phenyl which may be substituted with 1, 2, 3, 4, or 5 substituents R¹¹, wherein R¹¹ is as defined below; and a heteromonocyclic ring selected from rings of formulae F-1 to F-57 as defined in claim 32; wherein R⁸ is selected from OH, CN, C₃-C₈-cycloalkyl which optionally carries a CN or CF₃ substituent, C₃-C₈-halocycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, —C(═O)N(R^(102a))R^(102b), phenyl, optionally substituted with 1, 2, 3, 4 or 5 substituents R¹⁶, and a heterocyclic ring selected from rings of formulae E-1 to E-57 as defined in claim 25; wherein R^(102a), R^(102b), and R¹⁶ are as defined in claim 32; and each R¹¹ is independently selected from the group consisting of halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-haloalkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl, aminocarbonyl, C₁-C₄-alkylaminocarbonyl and di-(C₁-C₄-alkyl)-aminocarbonyl; or two R¹¹ present on the same carbon atom of a saturated heterocyclic ring may form together ═O or ═S; or two R¹¹ present on the same S or SO ring member of a heterocyclic ring may together form a group ═N(C₁-C₆-alkyl), ═NO(C₁-C₆-alkyl), ═NN(H)(C₁-C₆-alkyl) or ═NN(C₁-C₆-alkyl)₂.
 34. The method of claim 25, where the saturated heteromonocyclic ring R⁶ is selected from rings of formulae F-44-1 and F-53-1, and the heterocyclic ring R⁸ is selected from rings of formulae E-44-1 and E-57-1

wherein n is 0, 1 or 2; and R¹⁷ is selected from the group consisting of hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl and CH₂—(C₃-C₆-cycloalkyl).
 35. The method of claim 25, where B¹ is CR², where R² is not hydrogen, and B² and B³ are CR², where R² is selected from hydrogen, F, Cl, Br, OCF₃ and CF₃.
 36. The method of claim 25, where R⁴ is hydrogen.
 37. The method of claim 25, where R^(g1) and R^(g2) form together a bridging group —CH₂—CH₂—CH₂—.
 38. The method of claim 25, where R^(g1) and R^(g2) form together a bridging group —CH₂—CH₂—CH₂—CH₂—.
 39. The method of claim 25, where R^(3a) and R^(3b) are hydrogen or fluorine.
 40. The method of claim 25, of formula IB

wherein R^(2a) is Cl, R^(2b) is F, R^(2c) is Cl, and R⁶ is CH₂—C(O)—N(H)—R^(102b), wherein R^(102b) is selected from the group consisting of C₁-C₄-alkyl, C₂-C₄-alkyl substituted with 1 or 2 fluorine atoms, C₂-C₄-alkenyl, C₂-C₄-alkynyl, CH₂—CN, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl and C₃-C₆-cycloalkylmethyl; or an N-oxide, stereoisomer or veterinarily acceptable salt thereof.
 41. The method of claim 25, of formula IB as defined in claim 40, wherein R^(2a) is Cl, R^(2b) is F, R^(2c) is Cl, and R⁶ is —CH₂—R⁸, wherein R⁸ is selected from rings E-5, E-6, E-7, E-19, E-25, E-27, E-44-1 and E-57-1 as defined in claim 25, where the rings E-5, E-6, E-7, E-19 and E-27 are unsubstituted (k is 0) or carry 1 or 2 substituents R¹⁶ (k is 1 or 2), wherein each R¹⁶ is independently selected from halogen, cyano, nitro, C₁-C₂-alkyl, C₁-C₂-haloalkyl, C₁-C₂-alkoxy, C₁-C₂-haloalkoxy, C₁-C₂-alkylthio, C₁-C₂-haloalkylthio, C₁-C₂-alkylsulfinyl, C₁-C₂-haloalkylsulfinyl, C₁-C₂-alkylsulfonyl, C₁-C₂-haloalkylsulfonyl, C₃-C₄-cycloalkyl, C₃-C₄-halocycloalkyl, C₂-C₃-alkenyl, C₂-C₃-alkynyl; and where ring E-25 carries one substituent R¹⁶ on the nitrogen atom in the 1-position and optionally carries 1 or 2 further substituents R¹⁶, where R¹⁶ is as defined above; where however R¹⁶ bound in the 1-position is not is not halogen, cyano, nitro, C₁-C₂-alkoxy, C₁-C₂-haloalkoxy, C₁-C₂-alkylthio, C₁-C₂-haloalkylthio, C₁-C₂-alkylsulfinyl, C₁-C₂-haloalkylsulfinyl, C₁-C₂-alkylsulfonyl or C₁-C₂-haloalkylsulfonyl; or an N-oxide, stereoisomer or veterinarily acceptable salt thereof.
 42. The method of claim 25, of formula IB as defined in claim 40, wherein R^(2a) is Cl, R^(2b) is F, R^(2c) is Cl, and R⁶ is selected from rings F-2, F-4, F-6, F-8, F-9, F-44-1, F-46, F-51 and F-53-1 as defined in claim 32, where the rings F-2, F-4, F-6, F-8, F-9 and F-46 are unsubstituted (k is 0) or carry 1 or 2 substituents R¹¹ (k is 1 or 2), wherein each R¹¹ is independently selected from halogen, cyano, nitro, C₁-C₂-alkyl, C₁-C₂-haloalkyl, C₁-C₂-alkoxy, C₁-C₂-haloalkoxy, C₁-C₂-alkylthio, C₁-C₂-haloalkylthio, C₁-C₂-alkylsulfinyl, C₁-C₂-haloalkylsulfinyl, C₁-C₂-alkylsulfonyl, C₁-C₂-haloalkylsulfonyl, C₃-C₄-cycloalkyl, C₃-C₄-halocycloalkyl, C₂-C₃-alkenyl and C₂-C₃-alkynyl; and where ring F-51 is a ring of formula F-51-1

wherein R¹⁸ is selected from the group consisting of hydrogen, C₁-C₂-alkyl, C₁-C₂-haloalkyl, C₃-C₄-cycloalkyl, C₃-C₄-halocycloalkyl, C₂-C₃-alkenyl and C₂-C₃-alkynyl; or an N-oxide, stereoisomer or veterinarily acceptable salt thereof.
 43. The method of claim 25, of formula IB as defined in claim 40, wherein R^(2a) is Cl, R^(2b) is F, R^(2c) is Cl, and R⁶ is selected from C₂-C₄-alkyl which may be substituted with 1 or 2 fluorine atoms, cyclopropyl, C₃-C₅-halocycloalkyl, CH₂—(C₃-C₅-halocycloalkyl), CH₂-(1-cyano-(C₃-C₅-cycloalkyl)), C₂-C₄-alkenyl, C₂-C₄-alkynyl, CH₂—CN and —CH═NOR^(9a), wherein R^(9a) is selected from C₁-C₃-alkyl and C₁-C₃-haloalkyl; or an N-oxide, stereoisomer or veterinarily acceptable salt thereof.
 44. The method of claim 25, of formula IB as defined in claim 40, wherein R^(2a) is Cl, R^(2b) is F, R^(2c) is Cl, and R⁶ is N(H)R^(101b), wherein R^(101b) is selected from —C(O)—N(H)R^(14b) and rings E-1 and E-7 as defined in claim 25, where R^(14b) is selected from C₁-C₃-alkyl, C₁-C₃-haloalkyl and cyclopropyl; and where in rings E-1 and E-7 k is 0, 1 or 2; and each R¹⁶ is independently selected from halogen, cyano, nitro, C₁-C₂-alkyl, C₁-C₂-haloalkyl, C₁-C₂-alkoxy, C₁-C₂-haloalkoxy, C₁-C₂-alkylthio, C₁-C₂-haloalkylthio, C₁-C₂-alkylsulfinyl, C₁-C₂-haloalkylsulfinyl, C₁-C₂-alkylsulfonyl, C₁-C₂-haloalkylsulfonyl, C₃-C₄-cycloalkyl, C₃-C₄-halocycloalkyl, C₂-C₃-alkenyl, C₂-C₃-alkynyl; or an N-oxide, stereoisomer or veterinarily acceptable salt thereof. 